摘要：Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, GermanyInstitute of Organic Chemistry, RWTH Aachen University, Aache

转自：康龙化成

Copper-photoredox-catalysed C(sp3)–C(sp3) Reductive Cross-coupling of Alkyl Bromides with BCP-thianthrenium Reagents

Saikat Pandit and Tobias Ritter*

Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany Institute of Organic Chemistry, RWTH Aachen University, Aachen, Germany

—Angew. Chem. Int. Ed. 2025doi: 10.1002/anie.202506785.

Recommended by Bingbing Chang_ MC5

KEYWORDS:Cu catalysis, photo chemistry, reductive cross-coupling (反应类型),

C(sp3)-C(sp3) (成键类型), alkyl bromides, BCP-thianthrenium (反应物), alkyl-BCP (产物),2,3- bicyclo[1.1.1]pentane (BCP) (其他)

ABSTRACT:Prof. Tobias Ritter et al.report a reductive cross-coupling reaction of bicyclo[1.1.1]pentyl (BCP)-thianthrenium reagents and alkyl bromides. The reaction is catalysed by a copper/photoredox catalyst system. The approach is the first example of a cross-coupling between BCP-based reagents with alkyl electrophiles.

Proposed mechanism

Reaction development

Selected substrate scope of the reductive cross-coupling between alkyl bromides and BCP-thianthrenium salts

Synthesis of BCP analog of tesmilifene

Prof. Tobias Ritter et al.have described an efficient reductive cross-coupling reaction of alkyl bromides and BCP−TT+reagents, which yields a range of BCP-alkylated products through the formation of a C(sp3)−C(sp3) bond. It is noteworthy that their approach employed the dual/copper-photoredox condition for the coupling of two alkyl electrophiles, in contrast to the conventional use of nickel reductive conditions. They anticipate that their approach may facilitate the development of saturated analogs of diarylmethane drugs in the pharmaceutical industry.

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