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Selective Hydroarylation of 1,3‐Diynes Using a Dimeric Manganese Catalyst: Modular Synthesis of Z ‐Enynes
Author(s) -
Yan Zhongfei,
Yuan XiangAi,
Zhao Yue,
Zhu Chengjian,
Xie Jin
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201807851
Subject(s) - chemoselectivity , catalysis , chemistry , selectivity , combinatorial chemistry , transition metal , conjugated system , manganese , modular design , organic chemistry , computer science , polymer , operating system
The transition‐metal‐catalyzed selective hydroarylation of unsymmetrical alkynes represents the state‐of‐art in organic chemistry, and still mainly relies on the use of precious late‐transition‐metal catalysts. Reported herein is an unprecedented Mn I ‐catalyzed hydroarylation of unsymmetrical 1,3‐diyne alcohols with commercially available arylboronic acids with predictive selectivity. This method addresses the challenges in regio‐, stereo‐, and chemoselectivity. It offers a general, convenient and practical strategy for the modular synthesis of multisubstituted Z ‐configurated conjugated enynes. This protocol is distinguished by its operational simplicity, complete selectivity, excellent functional‐group compatibility, and gram‐scale potential. A dimeric Mn I species, Mn 2 (CO) 8 Br 2 , was proven to be a much more efficient catalyst precursor than Mn(CO) 5 Br.