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Synlett 2020; 31(12): 1221-1225
DOI: 10.1055/s-0040-1707946
letter
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Decarboxylative Methylation and Ethylation of Aliphatic N-(Acyloxy)phthalimides with Organoaluminum Reagents

Ze-Zhong Wang
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
,
Guang-Zu Wang
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
,
Bin Zhao
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
,
Rui Shang  ∗
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
b   Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan   Email: rui@chem.s.u-tokyo.ac.jp
,
Yao Fu∗
a   Hefei National Laboratory for Physical Sciences at the Microscale, CAS Key Laboratory of Urban Pollutant Conversion, Anhui Province Key Laboratory of Biomass Clean Energy, iChEM, Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China   Email: fuyao@ustc.edu.cn
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (21901237) and KY (2060000019). G.-Z.W. thanks the China Postdoctoral Science Foundation (2018M640588).
Further Information

Publication History

Received: 25 March 2020

Accepted after revision: 16 April 2020

Publication Date:
05 May 2020 (online)

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Abstract

A cobalt-catalyzed decarboxylative methylation of aliphatic redox-active esters [N-(acyloxy)phthalimides; RAEs] with trimethylaluminum under mild conditions was developed, providing a method for transforming a carboxylate group into a methyl group without redox fluctuation. Primary and secondary RAEs were both amenable substrates, whereas a tertiary RAE delivered an elimination product. Triethylaluminum was also used to deliver a decarboxylative ethylation product.

Key words

cobalt catalysis - decarboxylative methylation - ethylation - trimethylaluminum - redox-active esters

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1707946.
  • Supporting Information
 

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