NHC‐Au‐Catalyzed Isomerization of Propargylic B(MIDA)s to Allenes and Double Isomerization of Alkynes to 1,3‐Dienes

Author:

Liu Li‐Cai1,Lin Shuang1,Xu Kangwei1,Qian Jiasheng1,Wu Ruibo1,Li Qingjiang1,Wang Honggen1ORCID

Affiliation:

1. Guangdong Provincial Key Laboratory of Chiral Molecule and Drug Discovery School of Pharmaceutical Sciences Sun Yat‐Sen University Guangzhou 510006 China

Abstract

AbstractThe synthesis of allenyl boronates is an important yet challenging topic in organic synthesis. Reported herein is an NHC‐gold‐catalyzed 1,3‐H shift toward allenyl boronates synthesis from simple propargylic B(MIDA)s. Mechanistic studies suggest dual roles of the boryl moiety in the reaction: to activate the substrate for isomerization and at the same time, to prevent the allene product from further isomerization. These effects should be a result of α‐anion stabilization and α‐cation destabilization conferred by the B(MIDA) moiety, respectively. The NHC‐Au catalyst, which is commercially available, is also found to be reactive in alkyne‐to‐1,3‐diene isomerization reactions in an atom‐economic and base‐free manner.

Funder

National Natural Science Foundation of China

Guangdong Provincial Key Laboratory of Construction Foundation

Publisher

Wiley

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