Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis

Yoon Kyung Jang; Tobias Krückel; Magnus Rueping; Osama El-Sepelgy

doi:10.1021/acs.orglett.8b03184

Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis

Yoon Kyung Jang, Tobias Krückel, Magnus Rueping, Osama El-Sepelgy

Research output: Contribution to journal › Article › peer-review

71 Scopus citations

Abstract

The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.

Original language	English (US)
Pages (from-to)	7779-7783
Number of pages	5
Journal	Organic Letters
Volume	20
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.8b03184
State	Published - Dec 3 2018

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KAUST Repository Item: Exported on 2020-10-01

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10.1021/acs.orglett.8b03184

https://repository.kaust.edu.sa/bitstream/10754/630271/1/Manuscript.pdf

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title = "Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis",

abstract = "The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.",

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T1 - Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis

AU - Jang, Yoon Kyung

AU - Krückel, Tobias

AU - Rueping, Magnus

AU - El-Sepelgy, Osama

N1 - KAUST Repository Item: Exported on 2020-10-01

PY - 2018/12/3

Y1 - 2018/12/3

N2 - The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.

AB - The first example of manganese-catalyzed C-alkylation of the carboxylic acid derivatives is reported. The bench-stable homogeneous manganese complex enables the transformation of the renewable alcohol and carboxylic acid derivative feedstock to higher value esters and amides. The reaction operates via hydrogen autotransfer and ideally produces water as the only side product. Importantly, aliphatic-, benzylic-, and heterocyclic-containing alcohols can be used as alkylating reagents, eliminating the need for mutagenic alkyl halides.

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UR - https://pubs.acs.org/doi/10.1021/acs.orglett.8b03184

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JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Sustainable Alkylation of Unactivated Esters and Amides with Alcohols Enabled by Manganese Catalysis

Abstract

Bibliographical note

UN SDGs

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