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Palladium‐Catalyzed Decarboxylative Cross‐Couplings of 1‐Boc‐3‐iodoazetidine: Regioselective Access to 2‐Alkynylazetidines, 3‐Alkynylazetidines and 3‐Vinylazetidines
Author(s) -
Han Shuaijun,
Ren Xiaoxiao,
Wu Qingsong,
Liang Apeng,
Li Jingya,
Zou Dapeng,
Wu Yangjie,
Wu Yusheng
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800100
Subject(s) - regioselectivity , chemistry , palladium , catalysis , hydride , stereoselectivity , combinatorial chemistry , substrate (aquarium) , decarboxylation , organic chemistry , hydrogen , oceanography , geology
The first palladium‐catalyzed decarboxylative coupling reactions of alkynyl carboxylic acids or α, β‐unsaturated carboxylic acids with 1‐Boc‐3‐iodoazetidine were described. The strategy could efficiently mediate β‐hydride elimination/migratory insertion sequence and selectively form 2‐alkynylazetidines (10 examples) and 3‐alkynylazetidines (15 examples) with high regioselectivity. The protocol provides convienient access to a variety of useful 3‐vinylazetidines in moderate yields (42%–72%) with good stereoselectivity. Notable advantages of this method include easy operation, mild reaction conditions, and wide substrate scope.