Photoredox- and Cobalt-Cocatalyzed Dehydrogenative Ring-Opening/Functionalization of Monodonor Cyclopropanes

Abstract

Catalytic ring-opening/functionalization of unactive cyclopropanes has proven to be a significant but challenging task in organic synthesis. Herein, we disclose the photoredox and cobalt cocatalyzed ring-opening/acceptorless dehydrogenative functionalization of monodonor cyclopropanes, which provides a promising platform to achieve a sustainable and atom-economic approach to assemble allylic N-acyl-acetal derivatives. The reaction features mild conditions, broad substrate scopes, and excellent functional group compatibilities. The optimized conditions accommodate various cycloalkylamides and primary, secondary, and tertiary alcohols, with applications in late-stage functionalization of pharmaceutically relevant compounds, stimulating the further utility in medicinal chemistry. Selective nucleophilic substitutions and further transformations of desired products with various carbon nucleophiles were succeed in a one-pot fashion, thus offering diverse acyclic or cyclic derivatives.

1 Introduction

2 Cooperative Photoredox and Cobalt-Catalyzed Dehydrogenative Functionalization of Allylic N-Acyl-acetal Derivatives

3 Mechanistic Study

4 Preliminary Studies of Asymmetric Transformation

5 Conclusion and Perspectives

Key words

photoredox catalysis - cobaloxime catalysis - cyclopropane - ring opening - N,O-acetal

Publication History

Received: 31 May 2024

Accepted after revision: 11 June 2024

Accepted Manuscript online:
11 June 2024

Article published online:
25 June 2024

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