Issue 19, 2021

Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes

Abstract

Herein we report a nickel-catalyzed asymmetric reductive aryl-allylation of aryl iodide-tethered unactivated alkenes, wherein both acyclic allyl carbonates and cyclic vinyl ethylene carbonates can serve as the coupling partners. Furthermore, the direct use of allylic alcohols as the electrophilic allyl source in this reaction is also viable in the presence of BOC anhydride. Remarkably, this reaction proceeds with high linear/branched-, E/Z- and enantio-selectivity, allowing the synthesis of various chiral indanes and dihydrobenzofurans (50 examples) containing a homoallyl-substituted quaternary stereocenter with high optical purity (90–98% ee). In this reductive reaction, the use of pregenerated organometallics can be circumvented, giving this process good functionality tolerance and high step-economy.

Graphical abstract: Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes

Supplementary files

Article information

Article type
Edge Article
Submitted
25 Febr. 2021
Accepted
09 Apr. 2021
First published
09 Apr. 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 6712-6718

Nickel-catalyzed asymmetric reductive aryl-allylation of unactivated alkenes

Z. Lin, Y. Jin, W. Hu and C. Wang, Chem. Sci., 2021, 12, 6712 DOI: 10.1039/D1SC01115D

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