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Catalytic CN Bond Alkynylation of N ‐Benzylic Sulfonamides with Terminal Alkynes
Author(s) -
Liu Congrong,
Yang Fulai,
Wang Tingting
Publication year - 2014
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201400194
Subject(s) - chemistry , triple bond , regioselectivity , alkynylation , catalysis , medicinal chemistry , alkyne , propargyl , terminal (telecommunication) , sulfonamide , carbon fibers , combinatorial chemistry , double bond , organic chemistry , telecommunications , materials science , composite number , computer science , composite material
A new cross‐coupling reaction of N ‐benzylic sulfonamides with terminal alkynes for the synthesis of internal alkynes is reported. In the presence of 5 mol% of (Tf) 2 NH/Bi(OTf) 3 (1:1), a broad range of N ‐benzylic sulfonamides react smoothly with arylacetylenes to afford structurally diverse internal alkynes in moderate to excellent yields. We reasoned that vinyl cations could be formed by the regioselective attack of terminal alkynes with benzyl cations generated in situ from N ‐benzylic sulfonamides under acidic conditions, which then eliminated to form a carbon‐carbon triple bond.