Palladium-catalyzed asymmetric migratory diarylation of unactivated directing-group-free internal alkenes

Enantioselective dicarbofunctionalization of alkenes is a powerful strategy for constructing functionalized sp³-rich molecules, yet it remains challenging for unactivated substrates lacking directing groups. While asymmetric multicomponent reactions catalyzed by d¹⁰ transition metals have advanced for activated alkenes, enantioselective multicomponent cross-coupling of unactivated alkenes, particularly enabling remote functionalization to stereoselectively generate the nonadjacent stereocenters, is still underdeveloped. Herein, we report a palladium-catalyzed asymmetric migratory dicarbofunctionalization of directing-group-free, trisubstituted unactivated alkenes. This method forges remote stereogenic centers, enabling both 1,3-diarylation and 1,4-diarylation with high enantioselectivity and diastereoselectivity. Mechanistic studies indicate a chain-walking process involving irreversible Pd-H migration, rationalizing the observed regiocontrol.

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Journal
Nature Communications
Published
2026-01-05
DOI
https://doi.org/10.1038/s41467-025-68006-7
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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0.00

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article

Palladium-catalyzed asymmetric migratory diarylation of unactivated directing-group-free internal alkenes

Wenyi Huang, Linlin Fan, Jingping Qu, Yifeng Chen et al.
Nature Communications
Catalytic C–H Functionalization Methods
article

Palladium-catalyzed asymmetric migratory diarylation of unactivated directing-group-free internal alkenes

Wenyi Huang, Linlin Fan, Jingping Qu, Yifeng Chen, Wei-Hong Zhu, Honglei Gu, Yang Xi
article en

Abstract

Enantioselective dicarbofunctionalization of alkenes is a powerful strategy for constructing functionalized sp³-rich molecules, yet it remains challenging for unactivated substrates lacking directing groups. While asymmetric multicomponent reactions catalyzed by d¹⁰ transition metals have advanced for activated alkenes, enantioselective multicomponent cross-coupling of unactivated alkenes, particularly enabling remote functionalization to stereoselectively generate the nonadjacent stereocenters, is still underdeveloped. Herein, we report a palladium-catalyzed asymmetric migratory dicarbofunctionalization of directing-group-free, trisubstituted unactivated alkenes. This method forges remote stereogenic centers, enabling both 1,3-diarylation and 1,4-diarylation with high enantioselectivity and diastereoselectivity. Mechanistic studies indicate a chain-walking process involving irreversible Pd-H migration, rationalizing the observed regiocontrol.

Nature CommunicationsVol. 17(1)
East China University of Science and Technology (CN), Shanghai Institute of Organic Chemistry (CN), Henan Normal University (CN)
National Natural Science Foundation of China, China Postdoctoral Science Foundation, East China University of Science and Technology, Science and Technology Commission of Shanghai Municipality, Project 211, Fundamental Research Funds for the Central Universities
Reduced inequalities
Openalex Percentile: Top 97%
Catalytic C–H Functionalization Methods
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