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Synlett 2019; 30(01): 12-20
DOI: 10.1055/s-0037-1610313
DOI: 10.1055/s-0037-1610313
synpacts
Manganese-Catalyzed Direct Olefination via an Acceptorless Dehydrogenative Coupling of Methyl Heteroarenes with Primary Alcohols
This work supported by IISER Kolkata (Start-up grant) and SERB (ECR/2016/001654).Further Information
Publication History
Received: 13 September 2018
Accepted after revision: 12 October 2018
Publication Date:
14 November 2018 (online)
Abstract
Synthesis of olefins utilizing different catalytic strategies is an emerging topic in organic chemistry. However, despite of tremendous progress in the field the direct olefination of C(sp3)–H bonds using primary alcohols via an acceptorless dehydrogenative coupling (ADC) is not developed. Such an ADC reaction is highly environmentally benign as it produces dihydrogen and water as the sole byproducts. The liberated dihydrogen can potentially be used as an energy source. In this Synpact article, we present the recent development of ADC reaction as a tool to make unsaturated molecules and a summary of our recently developed synthetic procedure for the preparation of olefins employing an ADC reaction of methyl heteroarenes with alcohols. The catalyst development using an earth’s abundant metal manganese and the scope of such reaction is discussed.
1 Introduction
2 The Acceptorless Dehydrogenative Coupling as a Tool to Make Unsaturated Molecules
3 Transition-Metal-Catalyzed Coupling of Alcohols with Methyl-Substituted Heteroarenes
4 Development of the Manganese Catalyst for the Olefination of Methyl-Substituted Heteroarenes
5 Scope and Limitation of the Manganese-Catalyzed Direct Olefination of Methyl-Substituted Heteroarenes
6 Mechanistic Studies and Proposed Mechanism
7 Conclusion
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