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Synfacts 2018; 14(10): 1053
DOI: 10.1055/s-0037-1610890
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Iridium/Copper-Catalyzed Asymmetric Radical Cyanoalkylation of Styrenes

Contributor(s):
Hisashi Yamamoto
,
Wataru Muramatsu
Sha W. Deng L. Ni S. Pan Y. Mei H. * Han J. * Nanjing University, P. R. of China
Merging Photoredox and Copper Catalysis: Enantioselective Radical Cyanoalkylation of Styrenes.

ACS Catal. 2018;
8: 7489-7494
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Publication History

Publication Date:
17 September 2018 (online)

 
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Key words

iridium catalysis - copper catalysis - photoredox reaction - cyanoalkylation - styrenes

Significance

Asymmetric radical reactions are a markedly enriched area of recent chemistry. The authors describe an iridium/copper-catalyzed asymmetric radical cyanoalkylation of styrenes with alkyl N-hydroxyphthalimide esters and trimethylsilyl cyanide.


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Comment

This iridium/copper-catalyzed protocol promotes a radical cyanoalkylation of a wide range of both styrenes and alkyl N-hydroxy­phthalimide esters with trimethylsilyl cyanide to afford the corresponding cyanides with good yields and with high enantioselectivities. Mechanistic studies indicated that the reaction proceeds via benzylic radical species.


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