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Copper‐Catalyzed Synthesis of Tetrasubstituted Allenes from Quaternary Ammonium Salts and Grignard Reagents
Author(s) -
Ma Shengming,
Liu Qi,
Tang Xinjun,
Cai Yujuan
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600620
Subject(s) - chemistry , reagent , catalysis , tetrahydrofuran , ammonium , organic chemistry , copper , grignard reagent , combinatorial chemistry , medicinal chemistry , solvent
Although the synthesis of allenes has made considerable progress, methods for tetrasubstituted allenes are still limited. In this paper, the CuBr 2 ‐catalyzed cross‐coupling reaction of Grignard reagents and propargylic ammonium salts in tetrahydrofuran at 60 °C under argon delivered tetrasubstituted allenes in good to excellent yields. The reaction is thought to proceed by an S N 2′ pathway.