Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones

被引：97

作者：

He, Weimin ^{[1
]}

Xie, Longyong ^{[1
]}

Xu, Yingying ^{[1
]}

Xiang, Jiannan ^{[1
]}

Zhang, Liming ^{[2
]}

机构：

[1] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Coll Chem & Chem Engn, Changsha 410082, Hunan, Peoples R China

[2] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 16期

基金：

美国国家科学基金会;

关键词：

ONE-POT SYNTHESIS; BOND FUNCTIONALIZATION; N-BROMOSUCCINIMIDE; 3+2 CYCLOADDITION; AU CATALYSIS; ACTIVATION; INSERTION; YLIDES; ACID; HETEROCYCLES;

D O I：

10.1039/c2ob25235j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha-Oxo gold carbenes generated via intermolecular oxidation of terminal alkynes are shown to be highly electrophilic and can effectively abstract halogen from halogenated solvents such as 1,2-dichloroethane or 1,2-dibromoethane. Chloro/bromomethyl ketones are prepared in moderate efficiencies in one step using Ph3PAuNTf2 as the catalyst and 8-methylquinoline N-oxide as the oxidant.

引用

页码：3168 / 3171

页数：4

共 61 条

[1]

Benitez D, 2009, NAT CHEM, V1, P482, DOI [10.1038/NCHEM.331, 10.1038/nchem.331]

[2] Gold-Catalyzed Carbon-Heteroatom Bond-Forming Reactions [J].

Corma, A. ;

Leyva-Perez, A. ;

Sabater, Maria J. .

CHEMICAL REVIEWS, 2011, 111 (03) :1657-1712

[3] Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes [J].

Cuenca, Ana B. ;

Montserrat, Sergi ;

Hossain, Kabir M. ;

Mancha, Gisela ;

Lledos, Agusti ;

Medio-Simon, Mercedes ;

Ujaque, Gregori ;

Asensio, Gregorio .

ORGANIC LETTERS, 2009, 11 (21) :4906-4909

[4] Gold-catalyzed efficient synthesis of azepan-4-ones via a two-step [5+2] annulation [J].

Cui, Li ;

Ye, Longwu ;

Zhang, Liming .

CHEMICAL COMMUNICATIONS, 2010, 46 (19) :3351-3353

[5] A Two-Step, Formal [4+2] Approach toward Piperidin-4-ones via Au Catalysis [J].

Cui, Li ;

Peng, Yu ;

Zhang, Liming .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (24) :8394-+

[6] Gold or No Gold: One-Pot Synthesis of Tetrahydrobenz[b]azepin-4-ones from Tertiary N-(But-3-ynyl)anilines [J].

Cui, Li ;

Zhang, Guozhu ;

Peng, Yu ;

Zhang, Liming .

ORGANIC LETTERS, 2009, 11 (06) :1225-1228

[7] Sulfonic acid functionalized silica:: A remarkably efficient heterogeneous reusable catalyst for α-monobromination of carbonyl compounds using N-bromosuccinimide [J].

Das, B ;

Venkateswarlu, K ;

Holla, H ;

Krishnaiah, M .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) :107-111

[8] Catalytic enantioselective C-H activation by means of metal-carbenoid-induced C-H insertion [J].

Davies, HML ;

Beckwith, REJ .

CHEMICAL REVIEWS, 2003, 103 (08) :2861-2903

[9] Intermolecular and Selective Synthesis of 2,4,5-Trisubstituted Oxazoles by a Gold-Catalyzed Formal [3+2] Cycloaddition [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Dumitrescu, Lidia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (38) :8931-8935

[10] Site-specific introduction of gold-carbenoids by intermolecular oxidation of ynamides or ynol ethers [J].

Davies, Paul W. ;

Cremonesi, Alex ;

Martin, Nicolas .

CHEMICAL COMMUNICATIONS, 2011, 47 (01) :379-381

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