Selective C-H activation of alipathic hydrocarbons under phase-transfer conditions

Peter R. Schreiner; Oliver Lauenstein; Igor V. Kolomitsyn; Suad Nadi; Andrey A. Fokin

doi:10.1002/(SICI)1521-3773(19980803)37:13/14<1895::AID-ANIE1895>3.0.CO;2-A

Selective C-H activation of alipathic hydrocarbons under phase-transfer conditions

Peter R. Schreiner, Oliver Lauenstein, Igor V. Kolomitsyn, Suad Nadi, Andrey A. Fokin

Natural Resources Research Institute

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

71 Scopus citations

Abstract

Bromination of alipathic hydrocarbons with NaOH/CBr₄ under phase-transfer conditions selectively gives the tertiary bromide. In the absence of a tertiary C-H bond in the molecule, a secondary bond will be activated (see reaction equation). This conceptionally new system for alipathic C-H activation very likely relies on the initiation of single-electron transfer followed by a radical substitution with unusually high regioselectivity.

Original language	English (US)
Pages (from-to)	1895-1897
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	37
Issue number	13-14
DOIs	https://doi.org/10.1002/(SICI)1521-3773(19980803)37:13/14<1895::AID-ANIE1895>3.0.CO;2-A
State	Published - Aug 3 1998

Keywords

Adamantane
C-H activation
Phase-transfer catalysis
Radicals
Single-electron transfer

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10.1002/(SICI)1521-3773(19980803)37:13/14<1895::AID-ANIE1895>3.0.CO;2-A

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title = "Selective C-H activation of alipathic hydrocarbons under phase-transfer conditions",

abstract = "Bromination of alipathic hydrocarbons with NaOH/CBr4 under phase-transfer conditions selectively gives the tertiary bromide. In the absence of a tertiary C-H bond in the molecule, a secondary bond will be activated (see reaction equation). This conceptionally new system for alipathic C-H activation very likely relies on the initiation of single-electron transfer followed by a radical substitution with unusually high regioselectivity.",

keywords = "Adamantane, C-H activation, Phase-transfer catalysis, Radicals, Single-electron transfer",

author = "Schreiner, {Peter R.} and Oliver Lauenstein and Kolomitsyn, {Igor V.} and Suad Nadi and Fokin, {Andrey A.}",

year = "1998",

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doi = "10.1002/(SICI)1521-3773(19980803)37:13/14<1895::AID-ANIE1895>3.0.CO;2-A",

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TY - JOUR

T1 - Selective C-H activation of alipathic hydrocarbons under phase-transfer conditions

AU - Schreiner, Peter R.

AU - Lauenstein, Oliver

AU - Kolomitsyn, Igor V.

AU - Nadi, Suad

AU - Fokin, Andrey A.

PY - 1998/8/3

Y1 - 1998/8/3

N2 - Bromination of alipathic hydrocarbons with NaOH/CBr4 under phase-transfer conditions selectively gives the tertiary bromide. In the absence of a tertiary C-H bond in the molecule, a secondary bond will be activated (see reaction equation). This conceptionally new system for alipathic C-H activation very likely relies on the initiation of single-electron transfer followed by a radical substitution with unusually high regioselectivity.

AB - Bromination of alipathic hydrocarbons with NaOH/CBr4 under phase-transfer conditions selectively gives the tertiary bromide. In the absence of a tertiary C-H bond in the molecule, a secondary bond will be activated (see reaction equation). This conceptionally new system for alipathic C-H activation very likely relies on the initiation of single-electron transfer followed by a radical substitution with unusually high regioselectivity.

KW - Adamantane

KW - C-H activation

KW - Phase-transfer catalysis

KW - Radicals

KW - Single-electron transfer

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U2 - 10.1002/(SICI)1521-3773(19980803)37:13/14<1895::AID-ANIE1895>3.0.CO;2-A

DO - 10.1002/(SICI)1521-3773(19980803)37:13/14<1895::AID-ANIE1895>3.0.CO;2-A

M3 - Article

AN - SCOPUS:0032479750

SN - 1433-7851

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 13-14

ER -

Selective C-H activation of alipathic hydrocarbons under phase-transfer conditions

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