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Palladium‐Catalyzed Dearomative Methoxyallylation of 3‐Nitroindoles with Allyl Carbonates
Author(s) -
Xie JiaHao,
Zheng Chao,
You ShuLi
Publication year - 2021
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202107139
Subject(s) - catalysis , nucleophile , alkoxide , palladium , chemistry , combinatorial chemistry , organic chemistry
Herein we report a Pd‐catalyzed dearomative methoxyallylation of 3‐nitroindoles with readily available allyl carbonates. Good yields (up to 86 %) and diastereoselectivity (up to >20:1 dr) are obtained for a wide range of substrates. The compatibility of gram‐scale synthesis and the relatively low catalyst loading (down to 1 mol % of [Pd]) enhance the practicality of this method. The kinetic experiments indicate that the rate‐determining step of this reaction is the nucleophilic attack of the alkoxide anion.