Enantioselective Double Carbonylation Enabled by High-Valent Palladium Catalysis

Palladium-catalyzed carbonylation reactions are efficient methods for synthesizing valuable molecules. However, realizing a carbonylation with excellent yield and chemo-, regio-, and enantioselectivities by classical low-valent palladium catalysis is highly challenging. Herein, we describe an enanti...

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Published in:Journal of the American Chemical Society 2022-11, Vol.144 (47), p.21800-21807
Main Authors: Han, Jian, Xiao, Bo, Sun, Tian-Yu, Wang, Min, Jin, Long, Yu, Wangzhi, Wang, Yuqin, Fang, Dong-Mei, Zhou, Yan, Wu, Xiao-Feng, Wu, Yun-Dong, Liao, Jian
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cited_by cdi_FETCH-LOGICAL-a301t-efff7fd67bb6f2a81881b1b1f942cd9257bf1fe8a6689e9f7f4513f25bf8de873
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container_end_page 21807
container_issue 47
container_start_page 21800
container_title Journal of the American Chemical Society
container_volume 144
creator Han, Jian
Xiao, Bo
Sun, Tian-Yu
Wang, Min
Jin, Long
Yu, Wangzhi
Wang, Yuqin
Fang, Dong-Mei
Zhou, Yan
Wu, Xiao-Feng
Wu, Yun-Dong
Liao, Jian
description Palladium-catalyzed carbonylation reactions are efficient methods for synthesizing valuable molecules. However, realizing a carbonylation with excellent yield and chemo-, regio-, and enantioselectivities by classical low-valent palladium catalysis is highly challenging. Herein, we describe an enantioselective carbonylation reaction using a high-valent palladium catalysis strategy and employing a chiral sulfoxide phosphine (SOP) ligand. This double aminocarbonylation reaction begins with the formation of a carbamoylpalladium­(II) species, which undergoes enantioselective oxidative addition with a cyclic diaryliodonium salt to generate a palladium­(IV) intermediate, followed by a second CO insertion and reductive elimination. The mechanism has been illustrated with experimental and computational studies.
doi_str_mv 10.1021/jacs.2c10559
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title Enantioselective Double Carbonylation Enabled by High-Valent Palladium Catalysis
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