Transmetal-Catalyzed Enantioselective Cross-Coupling Reaction of Racemic Secondary Benzylic Bromides with Organoaluminum Reagents

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• 作者：Hong Fang ; Zhiyong Yang ; Lijun Zhang ; Wei Wang ; Yimei Li ; Xiaolong Xu ; Shuangliu Zhou
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：December 2, 2016
• 年：2016
• 卷：18
• 期：23
• 页码：6022-6025
• 全文大小：379K
• ISSN：1523-7052

文摘

The transmetal-catalyzed enantioselective cross-coupling reaction of secondary benzylic electrophiles with organoaluminum reagents has been developed. The reaction of secondary benzylic electrophiles with alkynylaluminum reagents provides a mild way for the chiral propargyl compounds bearing aromatic group in high yields with good enantioselectivities using NiBr₂·diglyme and (R)-iPr-Pybox as the catalytic system. The reaction of secondary benzylic electrophiles with alkenylaluminum reagents affords the corresponding chiral aryl alkenes in moderate yields with excellent stereoselectivities using commercially available PdCl₂ and (R)-BINAP as the catalytic system.