Palladium‐Catalyzed Decarboxylative Cross‐Couplings of 1‐Boc‐3‐iodoazetidine: Regioselective Access to 2‐Alkynylazetidines, 3‐Alkynylazetidines and 3‐Vinylazetidines. Issue 12 (2nd May 2018)

• Record Type: Journal Article
• Authors: Han, Shuaijun; Ren, Xiaoxiao; Wu, Qingsong; Liang, Apeng; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 12(2018)
• Page Start: 2308
• Page End: 2312
• Publication Date: 2018-05-02
• Subjects: β-hydride elimination -- migratory reinsertion -- decarboxylative coupling -- 1-Boc-3-iodoazetidine -- high regioselectivity; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201800100
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: 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. Abstract :