Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylatioin of Arenes

被引：113

作者：

Cuenca, Ana B. ^{[1
]}

Montserrat, Sergi ^{[2
]}

Hossain, Kabir M. ^{[1
]}

Mancha, Gisela ^{[1
]}

Lledos, Agusti ^{[2
]}

Medio-Simon, Mercedes ^{[1
]}

Ujaque, Gregori ^{[2
]}

Asensio, Gregorio ^{[1
]}

机构：

[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain

[2] Univ Autonoma Barcelona, Dept Quim, E-08193 Barcelona, Catalonia, Spain

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 21期

关键词：

HOMOGENEOUS GOLD CATALYSIS; AU CATALYSIS; PI-ACIDS; CYCLOISOMERIZATION; GENERATION; DIVERSITY; PLATINUM; CASCADE;

D O I：

10.1021/ol9020578

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 in good yields. Unpredictably, in all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom is obtained instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations is proposed to account for the products in this intermolecular gold(I)-catalyzed reaction.

引用

页码：4906 / 4909

页数：4

共 37 条

[1]

[Anonymous], 1964, FRIEDEL CRAFTS RELAT

[2] Alternative synthetic methods through new developments in catalysis by gold [J].

Arcadi, Antonio .

CHEMICAL REVIEWS, 2008, 108 (08) :3266-3325

[3]

Charton M., 1981, Progress in Physical Organic Chemistry, P119

[4]

CLEMENTI S, 1972, J CHEM SOC PERK T, V2, P71

[5] 1,2-alkyl migration as a key element in the invention of cascade reactions catalyzed by π-acids [J].

Crone, Benedikt ;

Kirsch, Stefan F. .

CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (12) :3514-3522

[6] 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-+

[7] 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

[8] Coinage metal catalyzed C-H bond functionalization of hydrocarbons [J].

Diaz-Requejo, M. Mar ;

Perez, Pedro J. .

CHEMICAL REVIEWS, 2008, 108 (08) :3379-3394

[9]

Dyker G, 2000, ANGEW CHEM INT EDIT, V39, P4237, DOI 10.1002/1521-3773(20001201)39:23<4237::AID-ANIE4237>3.0.CO

[10]

2-A

← 1 2 3 4 →