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Synlett 2021; 32(06): 573-581
DOI: 10.1055/s-0040-1707240
DOI: 10.1055/s-0040-1707240
account
Strategy for the Use of Molecular Oxygen in Organic Synthesis
Partial support from the Japan Society for the Promotion of Science (JSPS KAKENHI; Grant-in-Aid for Scientific Research (C), No. 19K06972) is gratefully acknowledged.Further Information
Publication History
Received: 02 June 2020
Accepted after revision: 10 July 2020
Publication Date:
24 August 2020 (online)
Abstract
Our recent studies on the development of new synthetic methods using molecular oxygen (O2), which is an environmentally friendly oxidant, are described in this Account. The character of O2 as an electron acceptor can be utilized for activation of simple organic molecules to generate reactive species. Such reactive species are applicable to advanced molecular transformation, such as C–C and C–X (X = heteroatom) bond formation, functionalization of inactivated C(sp3)–H, and catalytic Mitsunobu reaction, by avoiding direct quenching of the reactive species by O2.
1 Introduction
2 Reactions with Iron Catalysts and Oxygen
2.1 Reactions Using Redox Hydration of Alkenes
2.2 Reactions Using Oxidation of Heteroatoms
3 Reactions with tert-Butyl Nitrite and Oxygen
4 Conclusion
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Selected reviews on reactions with O2:
Recent reviews on iron catalysis:
Reviews on radical 1,5-HAT reactions:
Reviews on sulfonylation using sulfonyl hydrazides and others:
Selected reviews on Mitsunobu reactions: