Synthesis
DOI: 10.1055/a-1696-6429
short review

Recent Progress of Chromium-Mediated Carbonyl Addition Reactions

Yuri Katayama
1  Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan
,
Harunobu Mitsunuma
1  Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan
,
2  Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo, Japan
› Author Affiliations
Supported by: Japan Society for the Promotion of Science JP17H06441,JP17H06442,JP20H05843,JP21K15220

Organochromium(III) species are versatile nucleophiles in complex molecule synthesis due to their high functional group tolerance and chemoselectivity for aldehydes. Traditionally, carbonyl addition reactions of organochromium(III) species were performed through reduction of organohalides either using stoichiometric chromium(II) salts or catalytic chromium salts in the presence of stoichiometric reductants (such as manganese(0)). Recently, alternative methods emerged involving organoradical formation from readily available starting materials (e.g. N-hydroxyphthalimide esters, alkenes, and alkanes), followed by trapping the radical with stoichiometric or catalytic chromium(II) salts. Such methods, especially using catalytic chromium(II) salts, will lead to the development of sustainable chemical processes minimizing salt wastes and number of synthetic steps. In this review, we describe methods for generation of organochromium(III) species for addition reactions to carbonyl compounds, classified by nucleophiles.



Publication History

Received: 26 October 2021

Accepted after revision: 15 November 2021

Publication Date:
15 November 2021 (online)

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