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Copper‐Catalyzed Alkynylation of C( sp 3 )−H Bonds in N ‐Fluoro‐sulfonamides
Author(s) -
Yin Zhiping,
Zhang Youcan,
Zhang Shuo,
Wu XiaoFeng
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900992
Subject(s) - chemistry , catalysis , regioselectivity , acetylene , yield (engineering) , medicinal chemistry , copper , alkynylation , alkyne , organic chemistry , materials science , metallurgy
Herein, we developed a copper‐catalyzed approach for the remote C( sp 3 )−H alkynylation of N ‐fluoro‐sulfonamides. With Cu(OTf) 2 as the catalyst, the carbon radical which generated from nitrogen radical‐mediated 1,5‐hydrogen atom transfer, go through an addition/fragmentation reaction with various acetylene sulfones. A variety of internal alkynes were synthesized in high yield and regioselectivity. Notably, celecoxib‐derived substrate can also gave the corresponding functionalized product in good yield under the standard conditions.