共 96 条
Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions: role of the N-aryl substituent
被引:114
作者:

Collett, Christopher J.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

Massey, Richard S.
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h-index: 0
机构:
Univ Durham, Univ Sci Labs, Dept Chem, Durham DH1 3LE, England Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

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Batsanov, Andrei S.
论文数: 0 引用数: 0
h-index: 0
机构:
Univ Durham, Univ Sci Labs, Dept Chem, Durham DH1 3LE, England Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

O'Donoghue, AnnMarie C.
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h-index: 0
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Univ Durham, Univ Sci Labs, Dept Chem, Durham DH1 3LE, England Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

Smith, Andrew D.
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h-index: 0
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Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
机构:
[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland
[2] Univ Durham, Univ Sci Labs, Dept Chem, Durham DH1 3LE, England
基金:
英国工程与自然科学研究理事会;
关键词:
HETEROCYCLIC CARBENE;
ALPHA;
BETA-UNSATURATED ALDEHYDES;
TRIAZOLIUM SALTS;
NUCLEOPHILIC-ADDITION;
BRESLOW INTERMEDIATE;
THIAZOLIUM SALTS;
THIAMINE ACTION;
UMPOLUNG;
GENERATION;
ACID;
D O I:
10.1039/c2sc22137c
中图分类号:
O6 [化学];
学科分类号:
0703 ;
摘要:
The in situ observation, isolation and reversible formation of intermediate 3-(hydroxybenzyl) azolium salts derived from NHC addition to a range of substituted benzaldehydes is probed. Equilibrium constants for the formation of these 3-(hydroxybenzyl) azolium salts, as well as rate constants of hydrogen-deuterium exchange (k(ex)) at C(alpha) of these intermediates for a range of N-aryl triazolinylidenes is reported. These combined studies give insight into the preference of N-pentafluorophenyl NHCs to participate in benzoin and Stetter reaction processes.
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页码:1514 / 1522
页数:9
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