Bromination Functionalization of Diazo Compounds with CBr <sub>4</sub> via Convergent Paired Electrolysis

An electrochemical bromination of diazo compounds with CBr<sub>4</sub> as a bromine source via convergent paired electrolysis has been developed, which affords α-bromo phosphonates as products in up to 96% yields. This work represents the first example of direct anodic oxidation of diazos to couple with an <i>in situ</i>-generated nucleophile from the cationic reduction of CBr<sub>4</sub> by using CH<sub>2</sub>Cl<sub>2</sub> as a hydrogen source. This reaction features mild conditions, good substrate compatibility, and scale-up applicability, which represents a new electrochemical reaction mode of diazo compounds and also provides easy access to α-bromo phosphonates.

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Journal
Organic Letters
Published
2026-01-13
DOI
https://doi.org/10.1021/acs.orglett.5c05051
Primary Topic
Vanadium and Halogenation Chemistry
Type
article
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article

Bromination Functionalization of Diazo Compounds with CBr 4 via Convergent Paired Electrolysis

Jorge Escorihuela, Qi Wang, Jianlin Han, Romana Pajkert et al.
Organic Letters
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Bromination Functionalization of Diazo Compounds with CBr 4 via Convergent Paired Electrolysis

Jorge Escorihuela, Qi Wang, Jianlin Han, Romana Pajkert, Wentian Wu, Gerd-Volker Röschenthaler, Haibo Mei
article en

Abstract

An electrochemical bromination of diazo compounds with CBr<sub>4</sub> as a bromine source via convergent paired electrolysis has been developed, which affords α-bromo phosphonates as products in up to 96% yields. This work represents the first example of direct anodic oxidation of diazos to couple with an <i>in situ</i>-generated nucleophile from the cationic reduction of CBr<sub>4</sub> by using CH<sub>2</sub>Cl<sub>2</sub> as a hydrogen source. This reaction features mild conditions, good substrate compatibility, and scale-up applicability, which represents a new electrochemical reaction mode of diazo compounds and also provides easy access to α-bromo phosphonates.

Organic LettersVol. 28(3)
Universitat de València (ES), Nanjing Forestry University (CN), Constructor University (DE)
Openalex Percentile: Top 90%
Vanadium and Halogenation Chemistry
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