Electrochemical Synthesis of Dimeric λ3-Bromane: Platform for Hypervalent Bromine(III) Compounds

Igors Sokolovs; Edgars Sūna

doi:10.1021/acs.orglett.3c00405

Electrochemical Synthesis of Dimeric λ3-Bromane: Platform for Hypervalent Bromine(III) Compounds

Igors Sokolovs^*
, Edgars Sūna^*

^*Corresponding author for this work

Latvian Institute of Organic Synthesis

Research output: Contribution to journal › Article › peer-review

15 Citations (Scopus)

Abstract

A straightforward and scalable approach to a previously unreported class of cyclic hypervalent Br(III) species capitalizes on the anodic oxidation of aryl bromide to dimeric benzbromoxole that serves as a versatile platform to access a range of structurally diverse Br(III) congeners such as acetoxy-, alkoxy-, and ethynyl-λ³-bromanes as well as diaryl-λ³-bromanes. The synthetic utility of dimeric λ³-bromane is exemplified by photoinduced Minisci-type heteroarylation reactions and benzylic oxidation.

Original language	English
Pages (from-to)	2047-2052
Number of pages	6
Journal	Organic Letters
Volume	25
Issue number	12
DOIs	https://doi.org/10.1021/acs.orglett.3c00405
Publication status	Published - 31 Mar 2023

OECD Field of Science

1.4 Chemical Sciences

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10.1021/acs.orglett.3c00405

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abstract = "A straightforward and scalable approach to a previously unreported class of cyclic hypervalent Br(III) species capitalizes on the anodic oxidation of aryl bromide to dimeric benzbromoxole that serves as a versatile platform to access a range of structurally diverse Br(III) congeners such as acetoxy-, alkoxy-, and ethynyl-λ3-bromanes as well as diaryl-λ3-bromanes. The synthetic utility of dimeric λ3-bromane is exemplified by photoinduced Minisci-type heteroarylation reactions and benzylic oxidation.",

author = "Igors Sokolovs and Edgars Sūna",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

year = "2023",

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doi = "10.1021/acs.orglett.3c00405",

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AU - Sokolovs, Igors

AU - Sūna, Edgars

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Y1 - 2023/3/31

N2 - A straightforward and scalable approach to a previously unreported class of cyclic hypervalent Br(III) species capitalizes on the anodic oxidation of aryl bromide to dimeric benzbromoxole that serves as a versatile platform to access a range of structurally diverse Br(III) congeners such as acetoxy-, alkoxy-, and ethynyl-λ3-bromanes as well as diaryl-λ3-bromanes. The synthetic utility of dimeric λ3-bromane is exemplified by photoinduced Minisci-type heteroarylation reactions and benzylic oxidation.

AB - A straightforward and scalable approach to a previously unreported class of cyclic hypervalent Br(III) species capitalizes on the anodic oxidation of aryl bromide to dimeric benzbromoxole that serves as a versatile platform to access a range of structurally diverse Br(III) congeners such as acetoxy-, alkoxy-, and ethynyl-λ3-bromanes as well as diaryl-λ3-bromanes. The synthetic utility of dimeric λ3-bromane is exemplified by photoinduced Minisci-type heteroarylation reactions and benzylic oxidation.

UR - https://pubs.acs.org/doi/10.1021/acs.orglett.3c00405

UR - https://www.scopus.com/pages/publications/85151344928

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DO - 10.1021/acs.orglett.3c00405

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SP - 2047

EP - 2052

JO - Organic Letters

JF - Organic Letters

IS - 12

ER -

Electrochemical Synthesis of Dimeric λ3-Bromane: Platform for Hypervalent Bromine(III) Compounds

Abstract

OECD Field of Science

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