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Synthesis 2008(22): 3585-3590  
DOI: 10.1055/s-0028-1083216
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Kana Yamamoto, Kaori Tsurumi, Fumie Sakurai, Kazuhiro Kondo*, Toyohiko Aoyama*
Graduate School of Pharmaceutical Sciences, Nagoya City University, 3-1 Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan
e-Mail: kazuk@phar.nagoya-cu.ac.jp; e-Mail: aoyama@phar.nagoya-cu.ac.jp;
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Publication History

Received 14 July 2008
Publication Date:
10 November 2008 (online)

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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

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