Nickel-Catalyzed Asymmetric Reductive 1,4- and 1,5-Dicarbofunctionalization

Yutong Xiang; Chang Zhang; Chuan Wang

doi:10.1002/cjoc.202500074

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (11) :1271 -1278. DOI: 10.1002/cjoc.202500074

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Nickel-Catalyzed Asymmetric Reductive 1,4- and 1,5-Dicarbofunctionalization

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Abstract

Herein, we present the first examples of asymmetric reductive 1,4-dicarbofunctionalization of 1,3-dienes and 1,5-dicarbofunctionalization of vinylcyclopropanes, which proceed under the catalysis of a chiral nickel/bis-imidazoline complex using alkyl halides and aryl iodides or alkenyl bromides as the electrophilic coupling partners. In these highly enantioselective transformations operating in a radical relay mechanism, the C(sp³)- and C(sp²)-type carbo-moieties are respectively installed on the terminal and internal position with a newly formed olefinic unit in high E-selectivity.

Keywords

Difunctionalization / Alkenes / Carbocycles / Small ring systems / Nickel / Cross-coupling / Asymmetric catalysis

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Yutong Xiang, Chang Zhang, Chuan Wang. Nickel-Catalyzed Asymmetric Reductive 1,4- and 1,5-Dicarbofunctionalization. Chinese Journal of Chemistry, 2025, 43(11): 1271-1278 DOI:10.1002/cjoc.202500074