TY - JOUR
T1 - Catalytic Hydrogenation of Thioesters, Thiocarbamates, and Thioamides
AU - Luo, Jie
AU - Rauch, Michael
AU - Avram, Liat
AU - Ben-David, Yehoshoa
AU - Milstein, David
N1 - Funding Information:
This research was supported by the European Research Council (ERC AdG 692775). We thank Prof. Sergey Semenov and Dr. Yutao Sang for their help during the project. M.R. acknowledges the Zuckerman STEM Leadership Program for a research fellowship. D.M. is the Israel Matz Professorial Chair of Organic Chemistry.
Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/12/30
Y1 - 2020/12/30
N2 - Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.
AB - Direct hydrogenation of thioesters with H2 provides a facile and waste-free method to access alcohols and thiols. However, no report of this reaction is documented, possibly because of the incompatibility of the generated thiol with typical hydrogenation catalysts. Here, we report an efficient and selective hydrogenation of thioesters. The reaction is catalyzed by an acridine-based ruthenium complex without additives. Various thioesters were fully hydrogenated to the corresponding alcohols and thiols with excellent tolerance for amide, ester, and carboxylic acid groups. Thiocarbamates and thioamides also undergo hydrogenation under similar conditions, substantially extending the application of hydrogenation of organosulfur compounds.
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U2 - 10.1021/jacs.0c10884
DO - 10.1021/jacs.0c10884
M3 - Article
C2 - 33332968
AN - SCOPUS:85098888201
VL - 142
SP - 21628
EP - 21633
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 52
ER -