CuI‐catalyzed direct synthesis of diaryl thioethers from aryl boronic acids and arylsulfonyl chlorides

A CuI‐catalyzed direct coupling of aryl boronic acids with arylsulfonyl chlorides for the preparation of diaryl thioethers was developed. The reaction is initiated by a PPh3 reduction of the arylsulfonyl chloride, followed by a CuI‐catalyzed C–S coupling with an aryl boronic acid. Various arylsulfon...

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Published inApplied organometallic chemistry Vol. 34; no. 2
Main Authors Huang, Keke, Yang, Min, Lai, Xiao‐Jing, Hu, Xin, Qiu, Guanyinsheng, Liu, Jin‐Biao
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.02.2020
Wiley Subscription Services, Inc
Subjects
Aromatic compounds
aryl boronic acid
arylsulfonyl chloride
Chemical synthesis
Chemistry
Chemistry, Applied
Chemistry, Inorganic & Nuclear
Chlorides
Coupling
Cu(I) catalysis
Iodides
Physical Sciences
Science & Technology
thioether
C-H BOND
NICKEL-CATALYST
SULFENYLATION
SULFUR
arylsulfonyl chloride
N-OXIDES
HIGHLY EFFICIENT
aryl boronic acid
CROSS-COUPLINGS
S BOND
thioether
TE BOND
Cu(I) catalysis
SULFONYL CHLORIDES
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Summary:A CuI‐catalyzed direct coupling of aryl boronic acids with arylsulfonyl chlorides for the preparation of diaryl thioethers was developed. The reaction is initiated by a PPh3 reduction of the arylsulfonyl chloride, followed by a CuI‐catalyzed C–S coupling with an aryl boronic acid. Various arylsulfonyl chlorides can directly serve as a sulfur source in this mild and efficient reaction giving the desired products in moderate to good yields. Moreover, this practical method has also been applied to the thioetherification of aryl iodides and acetylacetones. A CuI‐catalyzed direct coupling of aryl boronic acids with arylsulfonyl chlorides for the preparation of diaryl thioethers was developed.
ISSN:0268-2605
1099-0739
DOI:10.1002/aoc.5385