Enantioselective hydroxylation of benzylic C-H bonds by D4-symmetric chiral oxoruthenium porphyrins

Rui Zhang; Wing Yiu Yu; Tat Shing Lai; Chi Ming Che

doi:10.1039/a904100a

Enantioselective hydroxylation of benzylic C-H bonds by D₄-symmetric chiral oxoruthenium porphyrins

Rui Zhang
, Wing Yiu Yu
, Tat Shing Lai
, Chi Ming Che

Research output: Journal article publication › Journal article › Academic research › peer-review

105 Citations (Scopus)

Abstract

A D4-symmetric chiral dioxoruthenium(VI) porphyrin can effect stoichiometric and catalytic enantioselective hydroxylation of benzylic C-H bonds to give enantioenriched aryl alcohols, the highest ee of 76% being attained in the catalytic oxidation of 4-ethyltoluene with 2,6-dichloropyridine N-oxide as terminal oxidant; the oxidations proceed via a rate-limiting H-atom abstraction to germinate a benzylic radical intermediate.

Original language	English
Pages (from-to)	1791-1792
Number of pages	2
Journal	Chemical Communications
Issue number	18
DOIs	https://doi.org/10.1039/a904100a
Publication status	Published - 21 Sept 1999
Externally published	Yes

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/a904100a

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title = "Enantioselective hydroxylation of benzylic C-H bonds by D4-symmetric chiral oxoruthenium porphyrins",

abstract = "A D4-symmetric chiral dioxoruthenium(VI) porphyrin can effect stoichiometric and catalytic enantioselective hydroxylation of benzylic C-H bonds to give enantioenriched aryl alcohols, the highest ee of 76\% being attained in the catalytic oxidation of 4-ethyltoluene with 2,6-dichloropyridine N-oxide as terminal oxidant; the oxidations proceed via a rate-limiting H-atom abstraction to germinate a benzylic radical intermediate.",

author = "Rui Zhang and Yu, \{Wing Yiu\} and Lai, \{Tat Shing\} and Che, \{Chi Ming\}",

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AU - Zhang, Rui

AU - Yu, Wing Yiu

AU - Lai, Tat Shing

AU - Che, Chi Ming

PY - 1999/9/21

Y1 - 1999/9/21

N2 - A D4-symmetric chiral dioxoruthenium(VI) porphyrin can effect stoichiometric and catalytic enantioselective hydroxylation of benzylic C-H bonds to give enantioenriched aryl alcohols, the highest ee of 76% being attained in the catalytic oxidation of 4-ethyltoluene with 2,6-dichloropyridine N-oxide as terminal oxidant; the oxidations proceed via a rate-limiting H-atom abstraction to germinate a benzylic radical intermediate.

AB - A D4-symmetric chiral dioxoruthenium(VI) porphyrin can effect stoichiometric and catalytic enantioselective hydroxylation of benzylic C-H bonds to give enantioenriched aryl alcohols, the highest ee of 76% being attained in the catalytic oxidation of 4-ethyltoluene with 2,6-dichloropyridine N-oxide as terminal oxidant; the oxidations proceed via a rate-limiting H-atom abstraction to germinate a benzylic radical intermediate.

UR - https://www.scopus.com/pages/publications/0033592385

U2 - 10.1039/a904100a

DO - 10.1039/a904100a

M3 - Journal article

SN - 1359-7345

SP - 1791

EP - 1792

JO - Chemical Communications

JF - Chemical Communications

IS - 18

ER -

Enantioselective hydroxylation of benzylic C-H bonds by D₄-symmetric chiral oxoruthenium porphyrins

Abstract

ASJC Scopus subject areas

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