Ti-Catalyzed Radical Alkylation of Secondary and Tertiary Alkyl Chlorides Using Michael Acceptors

Xiangyu Wu, Wei Hao, Ke-Yin Ye, Binyang Jiang, Gisselle Pombar, Zhidong Song, Song Lin*

*Department of Chemistry and Chemical Biology, Cornell University, Ithaca, New York 14853, United States, Email: songlincornell.edu

X. Wu, W. Hao, K.-Y. Ye, B. Jiang, G. Pombar, Z. Song, Song Lin, J. Am. Chem. Soc., 2018, 140, 14836-14843.

DOI: 10.1021/jacs.8b08605

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Abstract

Ti^III catalysis enables a radical addition of unactivated 2° and 3° alkyl chlorides to electron-deficient alkenes, while primary alkyl chlorides or aryl bromides remain untouched. This method offers a new route to C-C bond formation that is complementary to existing protocols.

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proposed mechanism

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Key Words

1,4-additions, zinc

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ID: J48-Y2018