TY - JOUR
T1 - Ni-Catalyzed Aryl Sulfide Synthesis through an Aryl Exchange Reaction
AU - Isshiki, Ryota
AU - Kurosawa, Miki B.
AU - Muto, Kei
AU - Yamaguchi, Junichiro
N1 - Funding Information:
This work was supported by JSPS KAKENHI grant numbers JP JP19H02726 (to J.Y.), JP21K05079 and JP20H04829 (hybrid catalysis) (to K.M.), and JP19J23053 and a Waseda Research Institute for Science and Engineering Grant in Aid for Young Scientists (Early Bird) (to R.I.). This work was also partially supported by JST ERATO grant number JPMJER1901 (to J.Y.). We thank Dr. Kenta Kato (Waseda University) for assistance with X-ray crystallographic analysis. We also thank the National Institute of Health Sciences in Japan for the support of NMR measurements. The Materials Characterization Central Laboratory in Waseda University is acknowledged for the support of the HRMS measurement.
Publisher Copyright:
© 2021 The Authors. Published by American Chemical Society
PY - 2021/7/14
Y1 - 2021/7/14
N2 - A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.
AB - A Ni-catalyzed aryl sulfide synthesis through an aryl exchange reaction between aryl sulfides and a variety of aryl electrophiles was developed. By using 2-pyridyl sulfide as a sulfide donor, this reaction achieved the synthesis of aryl sulfides without using odorous and toxic thiols. The use of a Ni/dcypt catalyst capable of cleaving and forming aryl-S bonds was important for the aryl exchange reaction between 2-pyridyl sulfides and aryl electrophiles, which include aromatic esters, arenol derivatives, and aryl halides. Mechanistic studies revealed that Ni/dcypt can simultaneously undergo oxidative additions of aryl sulfides and aromatic esters, followed by ligand exchange between the generated aryl-Ni-SR and aryl-Ni-OAr species to furnish aryl exchanged compounds.
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U2 - 10.1021/jacs.1c04215
DO - 10.1021/jacs.1c04215
M3 - Article
C2 - 34181399
AN - SCOPUS:85110321588
SN - 0002-7863
VL - 143
SP - 10333
EP - 10340
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 27
ER -