Development of Asymmetric Nickel-Catalyzed Arylation of Aromatic Aldehydes with Arylboron Reagents

Abstract

The development of the nickel-catalyzed 1,2-addition of triarylboroxins to aromatic aldehydes in the presence of a phosphine ligand is described. This development allowed the asymmetric nickel­-catalyzed 1,2-addition of arylboron reagents to aromatic aldehydes­. The enantioselectivity is synthetically acceptable (up to 81% ee) using 1-naphthaldehyde and 2-substituted aromatic aldehydes as substrates. The results have enantioselectivity comparable to the best results reported by us for the rhodium-catalyzed arylation of aromatic aldehydes.

Key words

arylation - arylboron - aromatic aldehyde - triarylboroxin

References

• 1 For a recent review, see: Schmidt F. Stemmler RT. Rudolph J. Bolm C. Chem. Soc. Rev.  2006,  35:  454 
• 2 Sakai M. Ueda M. Miyaura N. Angew. Chem. Int. Ed.  1998,  37:  3279 
• Other asymmetric Rh-catalyzed arylations of aromatic aldehydes with arylboronic acids:
• 3a Moreau C. Hague C. Weller AS. Frost CG. Tetrahedron Lett.  2001,  42:  6957 
• 3b Focken T. Rudolph J. Bolm C. Synthesis  2005,  429 
• 3c Suzuki K. Ishii S. Kondo K. Aoyama T. Synlett  2006,  648 
• 3d Suzuki K. Kondo K. Aoyama T. Synthesis  2006,  1360 
• 3e Arao T. Sato K. Kondo K. Aoyama T. Chem. Pharm. Bull.  2006,  54:  1576 
• 3f Arao T. Suzuki K. Kondo K. Aoyama T. Synthesis  2006,  3809 
• 3g For a Rh-catalyzed asymmetric arylation of a ketone group in isatins, see: Shintani R. Inoue M. Hayashi T. Angew. Chem. Int. Ed.  2006,  45:  3353 
• 4a Yamamoto T. Ohta T. Ito Y. Org. Lett.  2005,  7:  4153 
• 4b Suzuki K. Arao T. Ishii S. Maeda Y. Kondo K. Aoyama T. Tetrahedron Lett.  2006,  47:  5789 
• 4c He P. Lu Y. Dong C.-G. Hu Q.-S. Org. Lett.  2007,  9:  343 
• 4d Novodomska A. Dudicova M. Leroux FR. Colobert F. Tetrahedron: Asymmetry  2007,  18:  1628 
• 4e Shirai R. Shimazawa R. Kuriyama M. J. Org. Chem.  2008,  73:  1597 
• 5a Takahashi G. Shirakawa E. Tsuchimoto T. Kawakami Y. Chem. Commun.  2005,  1459 
• 5b For recent contributions of Ni-catalyzed addition to aldehydes, see: Ni-catalyzed alkylation of aldehydes with trialkylborane: Hirao K. Yorimitsu H. Oshima K. Org. Lett.  2005,  7:  4689 
• 5c Mahandru GM. Liu G. Montgomery J. J. Am. Chem. Soc.  2004,  126:  3698 
• 5d Miller KM. Huang W.-S. Jamison TF. J. Am. Chem. Soc.  2003,  125:  3442 
• 6 For our preliminary communication see: Arao T. Kondo K. Aoyama T. Tetrahedron Lett.  2007,  48:  4115 
• 7 For a recent review, see: Darses S. Genet JP. Chem. Rev.  2008,  108:  288 
• η^²-Coordinated nickel complexes with aldehydes have been reported:
• 8a Ogoshi S. Oka M. Kurosawa H. J. Am. Chem. Soc.  2004,  126:  11802 
• 8b Ogoshi S. Kamada H. Kurosawa H. Tetrahedron  2006,  62:  7583 
• 9a Tomita D. Wada R. Kanai M. Shibasaki M. J. Am. Chem. Soc.  2005,  127:  4138 
• 9b Tomita D. Kanai M. Shibasaki M. Chem. Asian J.  2006,  1-2:  161 
• 10 Bolm C. Rudolph J. J. Am. Chem. Soc.  2002,  124:  14850 
• 11 For new tuned Duphos derivatives, see: Oisaki K. Zhao D. Suto Y. Kanai M. Shibasaki M. Tetrahedron Lett.  2005,  46:  4325 
• 12 Ohkuma T. Koizumi M. Ikehira H. Yokozawa T. Noyori R. Org. Lett.  2000,  2:  659 
• 13 Wu X. Liu XX. Zhao G. Tetrahedron: Asymmetry  2005,  16:  2299 
• 14 Sharshira EM. Okamura M. Hasegawa E. Horaguchi T. J. Heterocycl. Chem.  1997,  34:  861