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
Key words manganese - acceptorless dehydrogenative coupling - NNN pincer ligand - olefination
- methyl heteroarenes
