Hydrogen-Bonding Controlled Nickel-Catalyzed Regioselective Cyclotrimerization of Terminal Alkynes
- 10 May 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (10), 3933-3938
- https://doi.org/10.1021/acs.orglett.1c01095
Abstract
Herein we report a hydrogen-bonding controlled nickel-catalyzed regioselective cyclotrimerization of terminal alkynes in moderate to excellent yields with high regioselectivities toward 1,3,5-trisubstituted benzenes. This method features a cheap catalyst, mild reaction conditions, and excellent functional group compatibility. The Ni–B(OH)2 complex in situ generated from NiCl2·DME and tetrahydroxydiboron might act as an active catalyst. After three consecutive cis-additions of terminal alkynes, internal migratory insertion cyclization, and β-boron elimination induced aromatization, 1,3,5-trisubstituted benzenes were selectively established.Keywords
Funding Information
- Natural Science Foundation of Tianjin City (19JCYBJC20200)
- Ministry of Science and Technology of the People's Republic of China (2017ZX07402003)
- Tianjin University
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