α‑Bromoacetate as a Mild and Safe Brominating Agent in the Light-Driven Vicinal Dibromination of Unactivated Alkenes and Alkynes

Harshvardhan Singh; Supuni I.N. Hewa Inaththappulige; Raj K. Tak; Ramesh Giri

doi:10.1021/acs.orglett.4c01778

α‑Bromoacetate as a Mild and Safe Brominating Agent in the Light-Driven Vicinal Dibromination of Unactivated Alkenes and Alkynes

Harshvardhan Singh
, Supuni I.N. Hewa Inaththappulige
, Raj K. Tak
, Ramesh Giri

Chemistry

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

6 Scopus citations

Abstract

Light-induced vicinal dibromination of unactivated alkenes and alkynes has been demonstrated by using methyl αbromoacetate as a mild brominating agent. A near-visible light (370 nm) light-emitting diode (LED) mediates this simple dibromination reaction under mild conditions with the inexpensive and nontoxic α-bromoacetate. The reaction proceeds well with both terminal and internal alkenes and alkynes and those contained in N/O-heterocycles, indicating its versatility in synthesizing dibrominated organic compounds.

Original language	English (US)
Pages (from-to)	5478-5481
Number of pages	4
Journal	Organic Letters
Volume	26
Issue number	26
DOIs	https://doi.org/10.1021/acs.orglett.4c01778
State	Published - Jul 5 2024

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.4c01778

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title = "α‑Bromoacetate as a Mild and Safe Brominating Agent in the Light-Driven Vicinal Dibromination of Unactivated Alkenes and Alkynes",

abstract = "Light-induced vicinal dibromination of unactivated alkenes and alkynes has been demonstrated by using methyl αbromoacetate as a mild brominating agent. A near-visible light (370 nm) light-emitting diode (LED) mediates this simple dibromination reaction under mild conditions with the inexpensive and nontoxic α-bromoacetate. The reaction proceeds well with both terminal and internal alkenes and alkynes and those contained in N/O-heterocycles, indicating its versatility in synthesizing dibrominated organic compounds.",

author = "Harshvardhan Singh and \{Hewa Inaththappulige\}, \{Supuni I.N.\} and Tak, \{Raj K.\} and Ramesh Giri",

note = "Publisher Copyright: {\textcopyright} 2024 American Chemical Society.",

year = "2024",

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doi = "10.1021/acs.orglett.4c01778",

language = "English (US)",

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T1 - α‑Bromoacetate as a Mild and Safe Brominating Agent in the Light-Driven Vicinal Dibromination of Unactivated Alkenes and Alkynes

AU - Singh, Harshvardhan

AU - Hewa Inaththappulige, Supuni I.N.

AU - Tak, Raj K.

AU - Giri, Ramesh

PY - 2024/7/5

Y1 - 2024/7/5

N2 - Light-induced vicinal dibromination of unactivated alkenes and alkynes has been demonstrated by using methyl αbromoacetate as a mild brominating agent. A near-visible light (370 nm) light-emitting diode (LED) mediates this simple dibromination reaction under mild conditions with the inexpensive and nontoxic α-bromoacetate. The reaction proceeds well with both terminal and internal alkenes and alkynes and those contained in N/O-heterocycles, indicating its versatility in synthesizing dibrominated organic compounds.

AB - Light-induced vicinal dibromination of unactivated alkenes and alkynes has been demonstrated by using methyl αbromoacetate as a mild brominating agent. A near-visible light (370 nm) light-emitting diode (LED) mediates this simple dibromination reaction under mild conditions with the inexpensive and nontoxic α-bromoacetate. The reaction proceeds well with both terminal and internal alkenes and alkynes and those contained in N/O-heterocycles, indicating its versatility in synthesizing dibrominated organic compounds.

UR - https://www.scopus.com/pages/publications/85197540922

UR - https://www.scopus.com/pages/publications/85197540922#tab=citedBy

U2 - 10.1021/acs.orglett.4c01778

DO - 10.1021/acs.orglett.4c01778

M3 - Article

C2 - 38917275

AN - SCOPUS:85197540922

SN - 1523-7060

VL - 26

SP - 5478

EP - 5481

JO - Organic Letters

JF - Organic Letters

IS - 26

ER -

α‑Bromoacetate as a Mild and Safe Brominating Agent in the Light-Driven Vicinal Dibromination of Unactivated Alkenes and Alkynes

Abstract

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