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Nickel‐Catalyzed Sulfonylation of C( sp 2 )–H Bonds with Sodium Sulfinates
Author(s) -
Liu ShuangLiang,
Li XueHong,
Zhang ShuSheng,
Hou ShengKai,
Yang GuangChao,
Gong JunFang,
Song MaoPing
Publication year - 2017
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.201700290
Subject(s) - chemistry , isopropylamine , nickel , catalysis , aryl , alkyl , functional group , medicinal chemistry , selectivity , sodium , amine gas treating , substrate (aquarium) , organic chemistry , stereochemistry , combinatorial chemistry , polymer , oceanography , geology
The first nickel‐catalyzed ortho ‐sulfonylation of C( sp 2 )–H bonds with sodium sulfinates directed by (pyridin‐2‐yl)isopropylamine (PIP‐amine) is described. This strategy exhibits a broad substrate scope and good functional group tolerance with high monosulfonylation selectivity. Besides arenes and heteroarenes, the reaction can also be extended to alkenes, providing diverse diaryl and alkyl aryl sulfones in high yields. Furthermore, a plausible Ni(I)/Ni(III) mechanism is outlined based on our experimental results and related precedents.