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Handbook of Functionalized Organometallics Applications in S

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References<br />

Nickel-catalyzed hydroam<strong>in</strong>ation <strong>of</strong> conjugated dienes at room temperature has<br />

been shown to be an efficient synthesis <strong>of</strong> allylam<strong>in</strong>es <strong>in</strong> excellent yields [262].<br />

10.10<br />

Conclusion<br />

+ HNMeBn Ni(COD) 2/DPPF, TFA<br />

94%<br />

NMeBn<br />

Over the past two decades,the use <strong>of</strong> organonickel chemistry <strong>in</strong> organic synthesis<br />

has evolved <strong>in</strong>to a new era. A wealth <strong>of</strong> fasc<strong>in</strong>at<strong>in</strong>g work has attested to the wide<br />

popularity us<strong>in</strong>g this metal <strong>in</strong> organic synthesis. Not only have the traditional<br />

cross-coupl<strong>in</strong>g reactions reached a new stage,but also new multi-component coupl<strong>in</strong>g<br />

processes have provided powerful arsenal for the synthesis <strong>of</strong> complex molecules.<br />

The mechanistic <strong>in</strong>sight <strong>of</strong> these reactions can pave the way to make predictions<br />

<strong>of</strong> other opportunities for new transformations and room for new <strong>in</strong>ventions<br />

emanat<strong>in</strong>g from the present results abound. In particular,given the reactivity<br />

trends <strong>of</strong> nickel reagents or catalysts and functional-group tolerance,such a prospect<br />

provides a major impetus for cont<strong>in</strong>u<strong>in</strong>g the use <strong>of</strong> organonickel compounds<br />

<strong>in</strong> organic synthesis.<br />

References<br />

1 For a review,see: Fischer,K.; Jonas,K.<br />

Misbach,P.; Stabba,R.; Wilke,G.<br />

Angew. Chem. Int. Ed. 1974, 12,<br />

943±953.<br />

2 Tamao,K.; Sumitani,K.; Kumada,M.<br />

J. Am. Chem. Soc. 1972, 94,4374±4376.<br />

3 Corriu,R. J. P.; Masse,J. P. J. Chem.<br />

Soc., Chem. Commun. 1972,144.<br />

4 Jolly,P. W.; Wilke,G. The Organic<br />

Chemistry <strong>of</strong>Nickel,Vols 1,2; Academic<br />

Press,New York,1974.<br />

5 Tetrahedron Symposia-<strong>in</strong>-Pr<strong>in</strong>t,No 69,<br />

Lipshutz,B. H.; Luh,T.-Y.,Eds. Tetrahedron<br />

1998, 54,1021±1316.<br />

6 For a recent review,see: Baudo<strong>in</strong>,O.;<br />

Gueritte,F. Stud. Nat. Prod. Chem.<br />

2003, 29, 355±417.<br />

7 Müllen,K.; Wegner,G. Electronic Materials:<br />

The Oligomer Approach; Wiley-VCH,<br />

1998.<br />

8 Hassan,J.; Sev<strong>in</strong>gnon,M.; Gozzi,C.;<br />

Schulz,E.; Lemaire,M. Chem. Rev.<br />

2002, 102,1359±1469.<br />

9 Nelson,T. D.; Crouch,R. D. Org. React.<br />

2004, 63,265±555.<br />

10 Semmelhack,M. F.; Helquist,P. M.;<br />

Jones,L. D. J. Am. Chem. Soc. 1971, 93,<br />

5908±5910.<br />

11 For a review,see: CaubØre,P. Angew.<br />

Chem. Int. Ed. 1983, 22,599±613.<br />

12 For synthetic applications <strong>of</strong> lithium<br />

naphthalide,see: Cohen,T.; Bhupathy,<br />

M. Acc. Chem. Res. 1989, 22,152±161.<br />

13 Duæach,E.; Franco,D.; Olivero,S. Eur.<br />

J. Org. Chem. 2003,1605±1622.<br />

14 Tomohiro,Y.; Satake,A.; Kobuke,Y.<br />

J. Org. Chem. 2001, 66,8442±8446.<br />

15 Kobuke,Y.; Ogawa,K. Bull. Chem. Jpn.<br />

2003, 76,689±708.<br />

16 Kondo,S.; Nagam<strong>in</strong>e,M.; Yano,Y.<br />

Tetrahedron Lett. 2004, 44,8801±8804.<br />

17 L<strong>in</strong>,G.-Q.; Hong,R. J. Org. Chem. 2001,<br />

66,2877±2880.<br />

18 Chen,C. Synlett 2000,1490±1492.<br />

19 Hu,Q.-S.; Zheng,X.-F.; L<strong>in</strong>,P. J. Org.<br />

Chem. 1996, 61,5200±5201.<br />

443

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