Handbook of Functionalized Organometallics Applications in S

More documents

Recommendations

Info

XVIII List of Authors Corinne Gosmini Laboratoire d'Electrochimie, Catalyse et Synth›se Organique 2 à 8, rue Henri-Dunant B. P. 28 94320 Thiais France Agn›s Herve Laboratoire de Chimie Organique et Organometallique UniversitØ de Bordeaux I 351, Cours de la Liberation 33405 Talence Cedex France Tamejiro Hiyama Department of Material Chemistry Graduate School of Engineering Kyoto University Kyoto University Katsura Nishikyo-ku Kyoto 615-8510 Japan Li-Fu Huang Institute of Chemistry Academia Sinica Nangang Taipei Taiwan 125 Hiriyakkanavar Ila Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Florian F. Kneisel Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Paul Knochel Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Alexander Koch KØkulØ-Institut für Organische Chemie und Biochemie Gerhard-Domagk-Strasse 1 53121 Bonn Germany Felix Kopp Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Tobias J. Korn Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Arkady Krasovskiy Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Helena Leuser Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany
Tien-Yau Luh Institute of Chemistry Academia Sinica Nangang Taipei Taiwan 125 Florence Mahuteau-Betzer Departement de Chimie, ESCOM UniversitØ de Paris 13, Boulevard de l'Hautil 95092 Cergy-Pontoise France Ilan Marek Department of Chemistry Technion-Israel Institute of Technology Technion City Haifa 32000 Israel Seijiro Matsubara Graduate School of Engineering Kyoto University Kyoutodaigaku-katsura Nishikyo Kyoto 615-8510 Japan Jacques PØrichon Laboratoire d'Electrochimie, Catalyse et Synth›se Organique 2 à 8, rue Henri-Dunant B. P. 28 94320 Thiais France Sylvie Perrone Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Ioannis Sapountzis Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany List of Authors Masaki Shimizu Department of Material Chemistry Graduate School of Engineering Kyoto University Kyoto University Katsura Nishikyo-ku Kyoto 615-8510 Japan G. Richard Stephenson Wolfson Materials and Catalysis Centre School of Chemical Sciences and Pharmacy University of East Anglia Norwich NR4 7TJ United Kingdom Martin Werner KØkulØ-Institut für Organische Chemie und Biochemie Gerhard-Domagk-Strasse 1 53121 Bonn Germany Xiaoyin Yang Department of Chemistry Ludwig-Maximilians-Universität Butenandtstrasse 5±13, Haus F 81377 München Germany Miguel Yus Departamento de Química Orgµnica Facultad de Ciencias and Instituto de Síntesis Orgµnica (ISO) Universidad de Alicante Apdo. 99 03080 Alicante Spain XIX
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 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 38 and 39: Li LiO 20 2 Polyfunctional Lithium
Page 40 and 41: Li 22 2 Polyfunctional Lithium Orga
Page 44 and 45: 26 Ph O Ni-Pr 2 2 Polyfunctional Li
Page 46 and 47: 28 Li 2 Polyfunctional Lithium Orga
Page 50 and 51: Li 32 203 2 Polyfunctional Lithium
Page 54 and 55: 36 Br 2 Polyfunctional Lithium Orga
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:
Page 72 and 73:
Ar H Ar = O HB O CF 3 CF 3 3.2 Prep
Page 74 and 75:
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:
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:
Page 92 and 93:
Page 94 and 95:
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:
Page 110 and 111:
Page 112 and 113:
Page 114 and 115:
Page 116 and 117:
R TrocO S N R 1 O S N 13 12 O 1 160
Page 118 and 119:
Page 120 and 121:
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:
Page 134 and 135:
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:
Page 142 and 143:
Page 144 and 145:
Cl MgBr 4.2Methods of Preparation o
Page 146 and 147:
Page 148 and 149:
Page 150 and 151:
Page 152 and 153:
Page 154 and 155:
Page 156 and 157:
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:
Page 164 and 165:
4.3 Further Applications of Functio
Page 166 and 167:
Page 168 and 169:
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:
Page 178 and 179:
Me OTf CO2Et + Me 4.4 Application o
Page 180 and 181:
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:
Page 272 and 273:
Page 274 and 275:
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:
Page 284 and 285:
Bu S O IZn(CH 2) 4ZnI 94 268 7 Poly
Page 286 and 287:
Page 288 and 289:
OAc MeO I EtO 2C 272 CHO S C N 7 Po
Page 290 and 291:
Page 292 and 293:
276 O 7 Polyfunctional Zinc Organom
Page 294 and 295:
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:
Page 304 and 305:
288 Ph N 214 O 7 Polyfunctional Zin
Page 306 and 307:
Page 308 and 309:
Page 310 and 311:
294 IZn AcO 7 Polyfunctional Zinc O
Page 312 and 313:
Page 314 and 315:
Page 316 and 317:
Page 318 and 319:
Page 320 and 321:
Page 322 and 323:
Page 324 and 325:
Page 326 and 327:
O 310 7 Polyfunctional Zinc Organom
Page 328 and 329:
Page 330 and 331:
Page 332 and 333:
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:
Page 344 and 345:
Page 346 and 347:
Page 348 and 349:
Page 350 and 351:
Page 352 and 353:
Page 354 and 355:
Page 356 and 357:
Page 358 and 359:
Page 360 and 361:
Page 362 and 363:
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:
Page 370 and 371:
Page 372 and 373:
Page 374 and 375:
Page 376 and 377:
Page 378 and 379:
CH 2(ZnI) 2 4 362 8 Polyfunctional
Page 380 and 381:
Page 382 and 383:
Page 384 and 385:
Page 386 and 387:
Page 388 and 389:
Page 390 and 391:
Page 392 and 393:
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:
Page 418 and 419:
Page 420 and 421:
Page 422 and 423:
Page 424 and 425:
Page 426 and 427:
Page 428 and 429:
Page 430 and 431:
Page 432 and 433:
Page 434 and 435:
Page 436 and 437:
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:
Page 444 and 445:
Page 446 and 447:
Page 448 and 449:
Page 450 and 451:
Page 452 and 453:
O 438 O Br 10 Functional Organonick
Page 454 and 455:
Page 456 and 457:
Cl 442 CN 10 Functional Organonicke
Page 458 and 459:
Page 460 and 461:
Page 462 and 463:
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:
Page 500 and 501:
Page 502 and 503:
Page 504 and 505:
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:
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:
Page 530 and 531:
R 1 O O O R R1 R 2 Scheme 12.28 R P
Page 532 and 533:
Page 534 and 535:
12.3 Functionalized Organotitanium
Page 536 and 537:
Page 538 and 539:
t-BuOOC Scheme 12.44 O CH 3 7.5 mol
Page 540 and 541:
Page 542 and 543:
H 13C 6 O R Scheme 12.52 SiMe 3 O T
Page 544 and 545:
Page 546 and 547:
O O OEt 87 Scheme 12.59 Scheme 12.6
Page 548 and 549:
Page 550 and 551:
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:
Page 586 and 587:
η5 η6 η4 η7 574 14 Polyfunction
Page 588 and 589:
Page 590 and 591:
Page 592 and 593:
Page 594 and 595:
Page 596 and 597:
Page 598 and 599:
Page 600 and 601:
Page 602 and 603:
Page 604 and 605:
Page 606 and 607:
51 594 CO 2Me + Fe(CO)3 CO2Me 14 Po
Page 608 and 609:
Page 610 and 611:
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:
Page 620 and 621:
Page 622 and 623:
Target molecule Disconnections Mult
Page 624 and 625:
Page 626 and 627:
Page 628 and 629:
Page 630 and 631:
Page 632 and 633:
Page 634 and 635:
Page 636 and 637:
Page 638 and 639:
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:
Page 658 and 659:
FG CuCN/LiCl ZnBr 0ºC CuZnBrCN 15.
Page 660 and 661:
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
show all

Handbook of Functionalized Organometallics Applications in S

Create successful ePaper yourself

Delete template?

Save as template?