Cross-Coupling Chemistry
at Mononuclear and Dinuclear Nickel Complexes

Sibo Lin; Theodor Agapie

doi:10.1055/s-0030-1259093

SYNPACTS

Cross-Coupling Chemistry at Mononuclear and Dinuclear Nickel Complexes

Sibo Lin, Theodor Agapie*
Division of Chemistry and Chemical Engineering, California Institute of Technology, MC127-72, 1200 E. California Blvd.,Pasadena, CA 91125, USA
Fax: +1(626)3956948; e-Mail: agapie@caltech.edu;

Abstract

All articles of this category

Abstract

Nickel catalysts have been developed for a wide range of C-C bond formation reactions. Reaction mechanisms proposed for these transformations generally involve catalytic intermediates based on mononickel species. These reactions are reviewed and the possibility of dinickel species active in C-C cross-coupling chemistry is discussed.

Key words

nickel - cross-coupling - alkyl halides - dinuclear mechanism - metal-arene interactions

Full Text

References

References and Notes

1a Metal-Catalyzed Cross-Coupling Reactions 2nd ed.: de Meijere A. Diederich F. Wiley-VCH; Weinheim: 2004.

1b Transition Metals for Organic Synthesis 2nd ed.: Beller M. Bolm C. Wiley-VCH; Weinheim: 2004.

2a Terao J. Kambe N. Acc. Chem. Res. 2008, 41: 1545

2b Netherton M. Fu G. Adv. Synth. Catal. 2004, 346: 1525

2c Rudolph A. Lautens M. Angew. Chem. Int. Ed. 2009, 48: 2656

2d Frisch AC. Beller M. Angew. Chem. Int. Ed. 2005, 44: 674

3a Kochi JK. Tamura M. J. Am. Chem. Soc. 1971, 93: 1483

3b Kochi JK. Tamura M. J. Am. Chem. Soc. 1971, 93: 1485

3c Tamao K. Hiyama T. Niegishi E.-i.
J. Organomet. Chem. 2002, 653: 1

3d Tamura M. Kochi JK. J. Am. Chem. Soc. 1971, 93: 1487

3e Uchino M. Yamamoto A. Ikeda S. J. Organomet. Chem. 1970, 24: C63

3f Yamamoto A. J. Organomet. Chem. 2002, 653: 5

4a Organometallic Mechanisms and Catalysis 1st ed.: Kochi JK. Academic Press, Inc.; New York: 1978.

4b Hatakeyama T. Hashimoto T. Kondo Y. Fujiwara Y. Seike H. Takaya H. Tamada Y. Ono T. Nakamura M. J. Am. Chem. Soc. 2010, 132: 10674

5a Devasagayaraj A. Stüdemann T. Knochel P. Angew. Chem. Int. Ed. Engl. 1996, 34: 2723

5b Giovannini R. Knochel P. J. Am. Chem. Soc. 1998, 120: 11186

5c Giovannini R. Studemann T. Devasagayaraj A. Dussin G. Knochel P. J. Org. Chem. 1999, 64: 3544

5d Giovannini R. Stüdemann T. Dussin G. Knochel P. Angew. Chem. Int. Ed. 1998, 37: 2387

6 Tasler S. Lipshutz BH. J. Org. Chem. 2002, 68: 1190

7 Terao J. Watanabe H. Ikumi A. Kuniyasu H. Kambe N. J. Am. Chem. Soc. 2002, 124: 4222

8a Jones GD. Martin JL. McFarland C. Allen OR. Hall RE. Haley AD. Brandon RJ. Konovalova T. Desrochers PJ. Pulay P. Vicic DA. J. Am. Chem. Soc. 2006, 128: 13175

8b Anderson TJ. Jones GD. Vicic DA. J. Am. Chem. Soc. 2004, 126: 8100

9a Lee J.-Y. Fu GC. J. Am. Chem. Soc. 2003, 125: 5616

9b Powell DA. Fu GC. J. Am. Chem. Soc. 2004, 126: 7788

10a Arp FO. Fu GC. J. Am. Chem. Soc. 2005, 127: 10482

10b Fischer C. Fu GC. J. Am. Chem. Soc. 2005, 127: 4594

10c Smith S. Fu G. Angew. Chem. Int. Ed. 2008, 47: 9334

10d Son S. Fu GC. J. Am. Chem. Soc. 2008, 130: 2756

11a Saito B. Fu GC. J. Am. Chem. Soc. 2007, 129: 9602

11b Saito B. Fu GC. J. Am. Chem. Soc. 2008, 130: 6694

11c Owston NA. Fu GC. J. Am. Chem. Soc. 2010, 132: 11908

12a Dai X. Strotman NA. Fu GC. J. Am. Chem. Soc. 2008, 130: 3302

12b González-Bobes F. Fu GC. J. Am. Chem. Soc. 2006, 128: 5360

12c Strotman N. Sommer S. Fu G. Angew. Chem. Int. Ed. 2007, 46: 3556

13 Lou S. Fu GC. J. Am. Chem. Soc. 2010, 132: 1264

14 Phapale V. Buñuel E. García-Iglesias M. Cárdenas D. Angew. Chem. Int. Ed. 2007, 46: 8790

15a Vechorkin O. Barmaz D. Proust V. Hu X. J. Am. Chem. Soc. 2009, 131: 12078

15b Csok Z. Vechorkin O. Harkins SB. Scopelliti R. Hu X. J. Am. Chem. Soc. 2008, 130: 8156

15c Vechorkin O. Csok Z. Scopelliti R. Hu X. Chem. Eur. J. 2009, 15: 3889

15d Vechorkin O. Hu X. Angew. Chem. Int. Ed. 2009, 48: 2937

15e Vechorkin O. Proust V. Hu X. J. Am. Chem. Soc. 2009, 131: 9756

16a Deprez NR. Sanford MS. J. Am. Chem. Soc. 2009, 131: 11234

16b Powers DC. Ritter T. Nat Chem. 2009, 1: 302

16c Powers DC. Xiao DY. Geibel MAL. Ritter T. J. Am. Chem. Soc. 2010, 132: 14530

17 Velian A. Lin S. Miller AJM. Day MW. Agapie T. J. Am. Chem. Soc. 2010, 132: 6296

18a Ramakrishna TVV. Sharp PR. Organometallics 2004, 23: 3079

18b Eisch JJ. Piotrowski AM. Han KI. Kruger C. Tsay YH. Organometallics 1985, 4: 224

19 Edelbach BL. Lachicotte RJ. Jones WD. Organometallics 1999, 18: 4040