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Handbook of Functionalized Organometallics Applications in S

Handbook of Functionalized Organometallics Applications in S

Handbook of Functionalized Organometallics Applications in

  • Page 2 and 3: Organometallics. Paul Knochel Copyr
  • Page 4 and 5: Handbook of Functionalized Organome
  • Page 6 and 7: Contents Preface XV List of Authors
  • Page 8 and 9: Contents 3.3.9 Oxidation of Functio
  • Page 10 and 11: 6.3.1 Nucleophilic Addition onto Ca
  • Page 12 and 13: 9.2.3 Preparation of Functionalized
  • Page 14 and 15: 13.6.4 Nickel-Catalyzed Cross-coupl
  • Page 16 and 17: Preface Since the pioneering work o
  • Page 18 and 19: XVIII List of Authors Corinne Gosmi
  • Page 20 and 21: 1 Introduction Paul Knochel and Fel
  • Page 22 and 23: umorganic is directly generated in
  • Page 24 and 25: Et H 21 Et AlBu 2 + CO 2Et Cu(CN)Mg
  • Page 26 and 27: 8 2 Polyfunctional Lithium Organome
  • Page 28 and 29: 10 2 Polyfunctional Lithium Organom
  • Page 30 and 31: R R 12 2 Polyfunctional Lithium Org
  • Page 32 and 33: MeO MeO R 14 2 Polyfunctional Lithi
  • Page 34 and 35: N 16 2 Polyfunctional Lithium Organ
  • Page 36 and 37: 18 2 Polyfunctional Lithium Organom
  • Page 38 and 39: Li LiO 20 2 Polyfunctional Lithium
  • Page 40 and 41: Li 22 2 Polyfunctional Lithium Orga
  • Page 42 and 43: 24 2 Polyfunctional Lithium Organom
  • Page 44 and 45: 26 Ph O Ni-Pr 2 2 Polyfunctional Li
  • Page 46 and 47: 28 Li 2 Polyfunctional Lithium Orga
  • Page 48 and 49: 30 2 Polyfunctional Lithium Organom
  • Page 50 and 51: Li 32 203 2 Polyfunctional Lithium
  • Page 52 and 53:

    34 2 Polyfunctional Lithium Organom

  • Page 54 and 55:

    36 Br 2 Polyfunctional Lithium Orga

  • Page 56 and 57:

    38 2 Polyfunctional Lithium Organom

  • Page 58 and 59:

    40 2 Polyfunctional Lithium Organom

  • Page 60 and 61:

    42 2 Polyfunctional Lithium Organom

  • Page 62 and 63:

    3 Functionalized Organoborane Deriv

  • Page 64 and 65:

    Br SSiMe 2tBu 4 3.2 Preparation and

  • Page 66 and 67:

    B O O 3.2 Preparation and Reaction

  • Page 68 and 69:

    3.2 Preparation and Reaction of Fun

  • Page 70 and 71:

    3.2 Preparation and Reaction of Fun

  • Page 72 and 73:

    Ar H Ar = O HB O CF 3 CF 3 3.2 Prep

  • Page 74 and 75:

    3.2 Preparation and Reaction of Fun

  • Page 76 and 77:

    X X Cl Cl TfO Cl 3.2 Preparation an

  • Page 78 and 79:

    HO HO Br OH O X N N O N 3.2 Prepara

  • Page 80 and 81:

    MOMO MOMO I CbzN O 3.2 Preparation

  • Page 82 and 83:

    3.2 Preparation and Reaction of Fun

  • Page 84 and 85:

    (HO) 3B O NMe 3 N N O Br 3.2 Prepar

  • Page 86 and 87:

    H H O O N H N H O OEt O O OEt O 3.2

  • Page 88 and 89:

    t BuO2C O N H 3.2 Preparation and R

  • Page 90 and 91:

    3.2 Preparation and Reaction of Fun

  • Page 92 and 93:

    3.2 Preparation and Reaction of Fun

  • Page 94 and 95:

    3.2 Preparation and Reaction of Fun

  • Page 96 and 97:

    R H2O R R B(OH) 2 B(OH) 2 3.3 Prepa

  • Page 98 and 99:

    3.3 Preparation and Reactions of Fu

  • Page 100 and 101:

    R 124 BF 3K Br 3.3 Preparation and

  • Page 102 and 103:

    B O O I OR O OR O O O O O OR 3.3 Pr

  • Page 104 and 105:

    S N O B O I O 133 3.4 Preparation a

  • Page 106 and 107:

    3.5 Synthesis and Reactions of Func

  • Page 108 and 109:

    3.7 Synthesis and Reactions of Func

  • Page 110 and 111:

    3.7 Synthesis and Reactions of Func

  • Page 112 and 113:

    3.7 Synthesis and Reactions of Func

  • Page 114 and 115:

    3.7 Synthesis and Reactions of Func

  • Page 116 and 117:

    R TrocO S N R 1 O S N 13 12 O 1 160

  • Page 118 and 119:

    3.7 Synthesis and Reactions of Func

  • Page 120 and 121:

    3.7 Synthesis and Reactions of Func

  • Page 122 and 123:

    22 H. Nakamura, M. Fujiwara, Y. Yam

  • Page 124 and 125:

    102 K. A. Scheidt, A. Tasaka, T. D.

  • Page 126 and 127:

    4 Polyfunctional Magnesium Organome

  • Page 128 and 129:

    crystallize with four-coordinated M

  • Page 130 and 131:

    4.2Methods of Preparation of Grigna

  • Page 132 and 133:

    4.2Methods of Preparation of Grigna

  • Page 134 and 135:

    4.2Methods of Preparation of Grigna

  • Page 136 and 137:

    NC Br Br 4.2Methods of Preparation

  • Page 138 and 139:

    N N Ph I 4.2Methods of Preparation

  • Page 140 and 141:

    4.2Methods of Preparation of Grigna

  • Page 142 and 143:

    4.2Methods of Preparation of Grigna

  • Page 144 and 145:

    Cl MgBr 4.2Methods of Preparation o

  • Page 146 and 147:

    4.2Methods of Preparation of Grigna

  • Page 148 and 149:

    4.2Methods of Preparation of Grigna

  • Page 150 and 151:

    4.2Methods of Preparation of Grigna

  • Page 152 and 153:

    4.2Methods of Preparation of Grigna

  • Page 154 and 155:

    4.2Methods of Preparation of Grigna

  • Page 156 and 157:

    4.2Methods of Preparation of Grigna

  • Page 158 and 159:

    O O O O 4.2Methods of Preparation o

  • Page 160 and 161:

    O Me Me O Pent I 4.2Methods of Prep

  • Page 162 and 163:

    4.2Methods of Preparation of Grigna

  • Page 164 and 165:

    4.3 Further Applications of Functio

  • Page 166 and 167:

    4.3 Further Applications of Functio

  • Page 168 and 169:

    4.3 Further Applications of Functio

  • Page 170 and 171:

    OTIPS I iPrMgCl OTIPS 4.3 Further A

  • Page 172 and 173:

    4.4 Application of Functionalized M

  • Page 174 and 175:

    I O O OBn Pd(t-Bu 3P) 2 (10 mol%) 4

  • Page 176 and 177:

    4.4 Application of Functionalized M

  • Page 178 and 179:

    Me OTf CO2Et + Me 4.4 Application o

  • Page 180 and 181:

    4.4 Application of Functionalized M

  • Page 182 and 183:

    12 a) F. Bickelhaupt in H. G. Riche

  • Page 184 and 185:

    56 G. Varchi, C. Kofink, D. M. Lind

  • Page 186 and 187:

    kin Trans. 1 1992, 1393; b) M. Sato

  • Page 188 and 189:

    31, 805; J. F. Hartwig, Angew. Chem

  • Page 190 and 191:

    5 Polyfunctional Silicon Organometa

  • Page 192 and 193:

    stereocontrol [5]. Similar chiral c

  • Page 194 and 195:

    5.2 Allylic Silanes seven-membered

  • Page 196 and 197:

    SiMe 3 33 Pr OH OSiMe 3 SiMe 3 34 O

  • Page 198 and 199:

    5.2 Allylic Silanes Although alkyl

  • Page 200 and 201:

    R O Si H 60a (R = H) 60b (R = Me) R

  • Page 202 and 203:

    Bpin SiMe 2Ph (CH 2) 2Ph 73 EtCH(OE

  • Page 204 and 205:

    BnO HO SiMe2Ph 2 BnO CHO BnO O BF3

  • Page 206 and 207:

    5.3 Alkenylsilanes When the same st

  • Page 208 and 209:

    HO I O Si Mo cat. : m n I O Si 111

  • Page 210 and 211:

    5.4Alkylsilanes Transition metal-ca

  • Page 212 and 213:

    5.4Alkylsilanes The fluoride-induce

  • Page 214 and 215:

    5.5 Miscellaneous Preparations and

  • Page 216 and 217:

    5.5 Miscellaneous Preparations and

  • Page 218 and 219:

    716. (c)I. E. Markó, J.-M. Planche

  • Page 220 and 221:

    6 Polyfunctional Tin Organometallic

  • Page 222 and 223:

    phine ligand or Pd II (PPh 3) 2Cl 2

  • Page 224 and 225:

    Bu 3 Sn Scheme 6.4 n-Pent + Me I O

  • Page 226 and 227:

    N N N H 2 I Scheme 6.8 N + Me Sn 3

  • Page 228 and 229:

    O O O NaO HO Me P O OH O OH (+)-Fos

  • Page 230 and 231:

    6.2 Metal-Catalyzed Coupling Reacti

  • Page 232 and 233:

    6.2 Metal-Catalyzed Coupling Reacti

  • Page 234 and 235:

    6.3 Nucleophilic Additions a-hydrox

  • Page 236 and 237:

    6.3 Nucleophilic Additions oxy alde

  • Page 238 and 239:

    6.3 Nucleophilic Additions found ap

  • Page 240 and 241:

    6.3 Nucleophilic Additions 6.3.1.5.

  • Page 242 and 243:

    6.3 Nucleophilic Additions ethylami

  • Page 244 and 245:

    N H 91% (ee:84%) Scheme 6.31 N CO 2

  • Page 246 and 247:

    6.4 Radical Reactions of Organotins

  • Page 248 and 249:

    TsN Scheme 6.37 + Bu 3Sn O Ph AIBN

  • Page 250 and 251:

    6.5.2 Tin-to-lithium Exchange 6.5.2

  • Page 252 and 253:

    Ar OR Scheme 6.42 N H SnBu 3 n-BuLi

  • Page 254 and 255:

    References 1 D. Azarian, S. S. Dua,

  • Page 256 and 257:

    Commun., 2002, 2608±2609; W. Su, S

  • Page 258 and 259:

    110 Y. Obora, M. Nakanishi, M. Toku

  • Page 260 and 261:

    178 Y. Yamamoto, H. Yatagai, Y. Nar

  • Page 262 and 263:

    J. Chem. Soc., Chem. Commun., 1995,

  • Page 264 and 265:

    301 D. P. G. Hamon, R. A. Massy-Wes

  • Page 266 and 267:

    371 I. D. Gridnev, O. L. Tok, N. A.

  • Page 268 and 269:

    252 7 Polyfunctional Zinc Organomet

  • Page 270 and 271:

    254 7 Polyfunctional Zinc Organomet

  • Page 272 and 273:

    256 7 Polyfunctional Zinc Organomet

  • Page 274 and 275:

    258 7 Polyfunctional Zinc Organomet

  • Page 276 and 277:

    BnO H Me 37 :1:1mixtureof diastereo

  • Page 278 and 279:

    262 Me 3Si 7 Polyfunctional Zinc Or

  • Page 280 and 281:

    264 F F 7 Polyfunctional Zinc Organ

  • Page 282 and 283:

    266 7 Polyfunctional Zinc Organomet

  • Page 284 and 285:

    Bu S O IZn(CH 2) 4ZnI 94 268 7 Poly

  • Page 286 and 287:

    270 7 Polyfunctional Zinc Organomet

  • Page 288 and 289:

    OAc MeO I EtO 2C 272 CHO S C N 7 Po

  • Page 290 and 291:

    274 7 Polyfunctional Zinc Organomet

  • Page 292 and 293:

    276 O 7 Polyfunctional Zinc Organom

  • Page 294 and 295:

    278 7 Polyfunctional Zinc Organomet

  • Page 296 and 297:

    280 E 7 Polyfunctional Zinc Organom

  • Page 298 and 299:

    282 MeO 2C O I 7 Polyfunctional Zin

  • Page 300 and 301:

    H Ph 284 7 Polyfunctional Zinc Orga

  • Page 302 and 303:

    286 7 Polyfunctional Zinc Organomet

  • Page 304 and 305:

    288 Ph N 214 O 7 Polyfunctional Zin

  • Page 306 and 307:

    290 7 Polyfunctional Zinc Organomet

  • Page 308 and 309:

    292 7 Polyfunctional Zinc Organomet

  • Page 310 and 311:

    294 IZn AcO 7 Polyfunctional Zinc O

  • Page 312 and 313:

    296 7 Polyfunctional Zinc Organomet

  • Page 314 and 315:

    298 7 Polyfunctional Zinc Organomet

  • Page 316 and 317:

    300 7 Polyfunctional Zinc Organomet

  • Page 318 and 319:

    302 7 Polyfunctional Zinc Organomet

  • Page 320 and 321:

    304 7 Polyfunctional Zinc Organomet

  • Page 322 and 323:

    306 7 Polyfunctional Zinc Organomet

  • Page 324 and 325:

    308 7 Polyfunctional Zinc Organomet

  • Page 326 and 327:

    O 310 7 Polyfunctional Zinc Organom

  • Page 328 and 329:

    312 7 Polyfunctional Zinc Organomet

  • Page 330 and 331:

    314 7 Polyfunctional Zinc Organomet

  • Page 332 and 333:

    316 7 Polyfunctional Zinc Organomet

  • Page 334 and 335:

    318 AcO 7 Polyfunctional Zinc Organ

  • Page 336 and 337:

    EtO 2C 320 MeO 7 Polyfunctional Zin

  • Page 338 and 339:

    MeO O 322 n-Hept O O I Me 7 Polyfun

  • Page 340 and 341:

    MeO 462 324 460 Br I 463 7 Polyfunc

  • Page 342 and 343:

    326 7 Polyfunctional Zinc Organomet

  • Page 344 and 345:

    328 7 Polyfunctional Zinc Organomet

  • Page 346 and 347:

    330 7 Polyfunctional Zinc Organomet

  • Page 348 and 349:

    332 7 Polyfunctional Zinc Organomet

  • Page 350 and 351:

    334 7 Polyfunctional Zinc Organomet

  • Page 352 and 353:

    336 7 Polyfunctional Zinc Organomet

  • Page 354 and 355:

    338 7 Polyfunctional Zinc Organomet

  • Page 356 and 357:

    340 7 Polyfunctional Zinc Organomet

  • Page 358 and 359:

    342 7 Polyfunctional Zinc Organomet

  • Page 360 and 361:

    344 7 Polyfunctional Zinc Organomet

  • Page 362 and 363:

    346 7 Polyfunctional Zinc Organomet

  • Page 364 and 365:

    348 8 Polyfunctional 1,1-Organodime

  • Page 366 and 367:

    350 O 8 Polyfunctional 1,1-Organodi

  • Page 368 and 369:

    352 8 Polyfunctional 1,1-Organodime

  • Page 370 and 371:

    354 8 Polyfunctional 1,1-Organodime

  • Page 372 and 373:

    356 8 Polyfunctional 1,1-Organodime

  • Page 374 and 375:

    358 8 Polyfunctional 1,1-Organodime

  • Page 376 and 377:

    360 8 Polyfunctional 1,1-Organodime

  • Page 378 and 379:

    CH 2(ZnI) 2 4 362 8 Polyfunctional

  • Page 380 and 381:

    364 8 Polyfunctional 1,1-Organodime

  • Page 382 and 383:

    366 8 Polyfunctional 1,1-Organodime

  • Page 384 and 385:

    368 8 Polyfunctional 1,1-Organodime

  • Page 386 and 387:

    370 8 Polyfunctional 1,1-Organodime

  • Page 388 and 389:

    372 8 Polyfunctional 1,1-Organodime

  • Page 390 and 391:

    374 8 Polyfunctional 1,1-Organodime

  • Page 392 and 393:

    376 8 Polyfunctional 1,1-Organodime

  • Page 394 and 395:

    9 Polyfunctional Organocopper Reage

  • Page 396 and 397:

    S 5 CuI·LiCl Cu(CN)Li Li naphthale

  • Page 398 and 399:

    Br CO 2Et I CO 2Et CO 2Et Np 2CuLi

  • Page 400 and 401:

    9.2 Preparation of Functionalized O

  • Page 402 and 403:

    Pent I O O Pent I CO 2Et O Br Pent

  • Page 404 and 405:

    Ph Ph N OMe 1) n-BuLi 2) alkynylcop

  • Page 406 and 407:

    9.3 Applications of Functionalized

  • Page 408 and 409:

    PrCu·MgBr 2·SMe 2 Pr Me H Pr H HO

  • Page 410 and 411:

    19 X. Yang, T. Rotter, C. Piazza, P

  • Page 412 and 413:

    n-C 7H 15 398 10 Functional Organon

  • Page 414 and 415:

    400 10 Functional Organonickel Reag

  • Page 416 and 417:

    402 10 Functional Organonickel Reag

  • Page 418 and 419:

    404 10 Functional Organonickel Reag

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    406 10 Functional Organonickel Reag

  • Page 422 and 423:

    408 10 Functional Organonickel Reag

  • Page 424 and 425:

    410 10 Functional Organonickel Reag

  • Page 426 and 427:

    412 10 Functional Organonickel Reag

  • Page 428 and 429:

    414 10 Functional Organonickel Reag

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    416 10 Functional Organonickel Reag

  • Page 432 and 433:

    418 10 Functional Organonickel Reag

  • Page 434 and 435:

    420 10 Functional Organonickel Reag

  • Page 436 and 437:

    422 10 Functional Organonickel Reag

  • Page 438 and 439:

    O 424 10 Functional Organonickel Re

  • Page 440 and 441:

    TIPSO R 1 Cp 2ClZr O H 426 O N 10 F

  • Page 442 and 443:

    428 10 Functional Organonickel Reag

  • Page 444 and 445:

    430 10 Functional Organonickel Reag

  • Page 446 and 447:

    432 10 Functional Organonickel Reag

  • Page 448 and 449:

    434 10 Functional Organonickel Reag

  • Page 450 and 451:

    436 10 Functional Organonickel Reag

  • Page 452 and 453:

    O 438 O Br 10 Functional Organonick

  • Page 454 and 455:

    440 10 Functional Organonickel Reag

  • Page 456 and 457:

    Cl 442 CN 10 Functional Organonicke

  • Page 458 and 459:

    444 10 Functional Organonickel Reag

  • Page 460 and 461:

    446 10 Functional Organonickel Reag

  • Page 462 and 463:

    448 10 Functional Organonickel Reag

  • Page 464 and 465:

    11 Polyfunctional Metal Carbenes fo

  • Page 466 and 467:

    11.2 Chromium-Templated Cycloadditi

  • Page 468 and 469:

    11.2 Chromium-Templated Cycloadditi

  • Page 470 and 471:

    (CO) 5Cr O Ph 15 1) t Bu t BuOMe, 5

  • Page 472 and 473:

    O MeO O O O O MeO O OMe Cr(CO) 5 Me

  • Page 474 and 475:

    11.2.3 Cyclization of Chromium Olig

  • Page 476 and 477:

    (CO)5Cr OR * O S + OMe 11.2 Chromiu

  • Page 478 and 479:

    [2+2+1] R 1 R 1 OH (CO) 5Cr R 2 (CO

  • Page 480 and 481:

    11.3 Reactions of Higher Nuclearity

  • Page 482 and 483:

    Br O X Br O R 2 R 2 O 85: X = Si-tB

  • Page 484 and 485:

    11.3 Reactions of Higher Nuclearity

  • Page 486 and 487:

    11.4 Metathesis Reactions Catalyzed

  • Page 488 and 489:

    R 2 R 1 O R O 3 O 11.4 Metathesis R

  • Page 490 and 491:

    i Pr i Pr i Pr Me Me (R)-160 Ph O O

  • Page 492 and 493:

    11.5 Transmetallation The dimerizat

  • Page 494 and 495:

    11.6 Metal Carbenes in Peptide Chem

  • Page 496 and 497:

    11.7 Stereoselective Syntheses with

  • Page 498 and 499:

    11.7 Stereoselective Syntheses with

  • Page 500 and 501:

    11.7 Stereoselective Syntheses with

  • Page 502 and 503:

    11.7 Stereoselective Syntheses with

  • Page 504 and 505:

    11.7 Stereoselective Syntheses with

  • Page 506 and 507:

    O O O O 100% H 2N O O O O O 311a Cr

  • Page 508 and 509:

    11.8 Sugar Metal Carbenes as Organo

  • Page 510 and 511:

    References zation reactions that al

  • Page 512 and 513:

    35 (a) C.A. Merlic, Y. You, D.M. Mc

  • Page 514 and 515:

    D. R. Cefalo, P. J. Bonitatebus Jr.

  • Page 516 and 517:

    12 Functionalized Organozirconium a

  • Page 518 and 519:

    12.2 Functionalized Organozirconoce

  • Page 520 and 521:

    Ph O (H)ZrCp Ph O 2Cl Ph O O O 92 %

  • Page 522 and 523:

    12.2 Functionalized Organozirconoce

  • Page 524 and 525:

    i-PrO O OBu-t O H N Scheme 12.15 H

  • Page 526 and 527:

    BnO Scheme 12.19 O BnO + 27 28 Cp 2

  • Page 528 and 529:

    12.2 Functionalized Organozirconoce

  • Page 530 and 531:

    R 1 O O O R R1 R 2 Scheme 12.28 R P

  • Page 532 and 533:

    12.2 Functionalized Organozirconoce

  • Page 534 and 535:

    12.3 Functionalized Organotitanium

  • Page 536 and 537:

    12.3 Functionalized Organotitanium

  • Page 538 and 539:

    t-BuOOC Scheme 12.44 O CH 3 7.5 mol

  • Page 540 and 541:

    12.3 Functionalized Organotitanium

  • Page 542 and 543:

    H 13C 6 O R Scheme 12.52 SiMe 3 O T

  • Page 544 and 545:

    12.3 Functionalized Organotitanium

  • Page 546 and 547:

    O O OEt 87 Scheme 12.59 Scheme 12.6

  • Page 548 and 549:

    12.3 Functionalized Organotitanium

  • Page 550 and 551:

    12.3 Functionalized Organotitanium

  • Page 552 and 553:

    40 A. M. Sun, X. Huang, Heteroatom

  • Page 554 and 555:

    13 Manganese Organometallics for th

  • Page 556 and 557:

    13.2.2 Preparation of Organomangane

  • Page 558 and 559:

    13.3 1,2-Addition to Aldehydes and

  • Page 560 and 561:

    13.3.2 Manganese-Mediated Barbier-

  • Page 562 and 563:

    HeptMnX + HeptMnX + Scheme 13.17 Cl

  • Page 564 and 565:

    13.4 Preparation of Ketones by Acyl

  • Page 566 and 567:

    Me 3Si Cl ( ) 3 R Li 80% 82% Scheme

  • Page 568 and 569:

    13.5 1,4-Addition of Organomanganes

  • Page 570 and 571:

    BuM BuMgCl BuMnCl BuMgCl BuCu BuCu

  • Page 572 and 573:

    13.6 Transition-Metal-Catalyzed Cro

  • Page 574 and 575:

    13.6 Transition-Metal-Catalyzed Cro

  • Page 576 and 577:

    I Cl Scheme 13.56 MeO MnCl (1.2 equ

  • Page 578 and 579:

    13.7 Manganese-Mediated Cross-coupl

  • Page 580 and 581:

    13 C. Boucley, G. Cahiez, unpublish

  • Page 582 and 583:

    570 14 Polyfunctional Electrophilic

  • Page 584 and 585:

    572 14 Polyfunctional Electrophilic

  • Page 586 and 587:

    η5 η6 η4 η7 574 14 Polyfunction

  • Page 588 and 589:

    576 14 Polyfunctional Electrophilic

  • Page 590 and 591:

    578 14 Polyfunctional Electrophilic

  • Page 592 and 593:

    580 14 Polyfunctional Electrophilic

  • Page 594 and 595:

    582 14 Polyfunctional Electrophilic

  • Page 596 and 597:

    584 14 Polyfunctional Electrophilic

  • Page 598 and 599:

    586 14 Polyfunctional Electrophilic

  • Page 600 and 601:

    588 14 Polyfunctional Electrophilic

  • Page 602 and 603:

    590 14 Polyfunctional Electrophilic

  • Page 604 and 605:

    592 14 Polyfunctional Electrophilic

  • Page 606 and 607:

    51 594 CO 2Me + Fe(CO)3 CO2Me 14 Po

  • Page 608 and 609:

    596 14 Polyfunctional Electrophilic

  • Page 610 and 611:

    598 14 Polyfunctional Electrophilic

  • Page 612 and 613:

    Table 14.1 Examples of synthetic ap

  • Page 614 and 615:

    602 Entry Target molecule Disconnec

  • Page 616 and 617:

    Entry Target molecule Disconnection

  • Page 618 and 619:

    Entry Target molecule Disconnection

  • Page 620 and 621:

    Entry Target molecule Disconnection

  • Page 622 and 623:

    Target molecule Disconnections Mult

  • Page 624 and 625:

    612 14 Polyfunctional Electrophilic

  • Page 626 and 627:

    614 14 Polyfunctional Electrophilic

  • Page 628 and 629:

    616 14 Polyfunctional Electrophilic

  • Page 630 and 631:

    618 14 Polyfunctional Electrophilic

  • Page 632 and 633:

    620 14 Polyfunctional Electrophilic

  • Page 634 and 635:

    622 14 Polyfunctional Electrophilic

  • Page 636 and 637:

    624 14 Polyfunctional Electrophilic

  • Page 638 and 639:

    626 14 Polyfunctional Electrophilic

  • Page 640 and 641:

    15 Polyfunctional Zinc, Cobalt and

  • Page 642 and 643:

    Trifluoromethylzinc compounds prepa

  • Page 644 and 645:

    15.3 Electrochemical Synthesis and

  • Page 646 and 647:

    15.3.2 Carbon±Carbon Bond Formatio

  • Page 648 and 649:

    Cl Cl NC + MeO2C 1eq 2eq e, CoX 2 c

  • Page 650 and 651:

    1eq Br FG + R 2eq OAc e, CoX 2 cat

  • Page 652 and 653:

    Cl O + O e, FeBr 2(Bpy) n DMF, Fe a

  • Page 654 and 655:

    15.4 Electrosynthesis of Compounds

  • Page 656 and 657:

    15.4 Electrosynthesis of Compounds

  • Page 658 and 659:

    FG CuCN/LiCl ZnBr 0ºC CuZnBrCN 15.

  • Page 660 and 661:

    15.4 Electrosynthesis of Compounds

  • Page 662 and 663:

    15.5 General Conclusion (industrial

  • Page 664 and 665:

    17 Durandetti, M.; Devaud, M.; Peri

  • Page 666 and 667:

    I2 Index b-alkoxyalkylidenemalonic,

  • Page 668 and 669:

    I4 Index boronic ester 47 4-boronyl

  • Page 670 and 671:

    I6 Index cyclohexadiene 415 cyclohe

  • Page 672 and 673:

    I8 Index fluoroalkenylstannane 206

  • Page 674 and 675:

    I10 Index iron-catalyzed carbolithi

  • Page 676 and 677:

    I12 Index nickel-catalyzed carbozin

  • Page 678 and 679:

    I14 Index psicosecarbene complexes

  • Page 680 and 681:

    I16 Index Suzuki-Miyaura reaction a

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