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The Palladium-Catalyzed Addition of Aryl- and Heteroarylboronic Acids to Aldehydes

Changming Qin, Huayue Wu,* Jiang Cheng,* Xi'an Chen, Miaochang Liu, Weiwei Zhang, Weike Su and Jinchang Ding

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325027, People's Republic of China, Email: huayuewuwzu.edu.cn, jiangchengwzu.edu.cn

C. Qin, H. Wu, J. Cheng, X. Chen, M. Liu, W. Zhang, W. Su, J. Ding, J. Org. Chem., 2007, 72, 4102-4107.

DOI: 10.1021/jo070267h (free Supporting Information)


Abstract

The 1,2-addition of aryl- or heteroarylboronic acids to aldehydes in the presence of PdCl2 and P(1-Nap)3 affords carbinol derivatives in very good yields. The reaction tolerates nitro, cyano, acetamido, acetoxy, acetyl, carboxyl, trifluoromethyl, fluoro, and chloro groups and allows the conversion of aliphatic aldehydes and hindered substrates.

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Key Words

1,2-addition, benzylic alcohols


ID: J42-Y2007-1610