Trichlorophenyl Formate: Highly Reactive and Easily Accessible Crystalline CO Surrogate for Palladium-Catalyzed Carbonylation of Aryl/Alkenyl Halides and Triflates

被引：122

作者：

Ueda, Tsuyoshi ^{[1
,2
]}

Konishi, Hideyuki ^{[1
]}

Manabe, Kei ^{[1
]}

机构：

[1] Univ Shizuoka, Sch Pharmaceut Sci, Suruga Ku, Shizuoka 4228526, Japan

[2] Daiichi Sankyo Co Ltd, Pharmaceut Technol Div, Proc Technol Res Labs, Hiratsuka, Kanagawa 2540014, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 20期

关键词：

CARBON-MONOXIDE; ARYL FORMATES; VINYL HALIDES; SYSTEM;

D O I：

10.1021/ol302593z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The high utility of 2,4,6-trichlorophenyl formate, a highly reactive and easily accessible crystalline CO surrogate, is demonstrated. The decarbonylation with NEt3 to generate CO proceeded rapidly at rt, thereby allowing external-CO-free Pd-catalyzed carbonylation of aryl/alkenyl halides and triflates. The high reactivity of the CO surrogate enabled carbonylation at rt and significantly reduced the quantities of formate to near-stoichiometric levels. The obtained trichlorophenyl esters can be readily converted to a variety of carboxylic acid derivatives in high yields.

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页码：5370 / 5373

页数：4

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共 21 条

[1] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds [J].

Brennfuehrer, Anne ;

Neumann, Helfried ;

Beller, Matthias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) :4114-4133

[2] Palladium-catalyzed hydroxycarbonylation of aryl and vinyl halides or triflates by acetic anhydride and formate anions [J].

Cacchi, S ;

Fabrizi, G ;

Goggiamani, A .

ORGANIC LETTERS, 2003, 5 (23) :4269-4272

[3] A NOVEL AND CONVENIENT METHOD FOR PALLADIUM-CATALYZED ALKOXYCARBONYLATION OF ARYL AND VINYL HALIDES USING HCO2R/NAOR SYSTEM [J].

CARPENTIER, JF ;

CASTANET, Y ;

BROCARD, J ;

MORTREUX, A ;

PETIT, F .

TETRAHEDRON LETTERS, 1991, 32 (36) :4705-4708

[4] An efficient conversion of phenolic esters to benzothiazoles under mild and virtually neutral conditions [J].

Chakraborti, AK ;

Rudrawar, S ;

Kaur, G ;

Sharma, L .

SYNLETT, 2004, (09) :1533-1536

[5] Synthesis and evaluation of quinoline carboxyguanidines as antidiabetic agents [J].

Edmont, D ;

Rocher, R ;

Plisson, C ;

Chenault, J .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (16) :1831-1834

[6] Silacarboxylic Acids as Efficient Carbon Monoxide Releasing Molecules: Synthesis and Application in Palladium-Catalyzed Carbonylation Reactions [J].

Friis, Stig D. ;

Taaning, Rolf H. ;

Lindhardt, Anders T. ;

Skrydstrup, Troels .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (45) :18114-18117

[7] Palladium-catalyzed esterification of aryl halides using aryl formates without the use of external carbon monoxide [J].

Fujihara, Tetsuaki ;

Hosoki, Tomoya ;

Katafuchi, Yuko ;

Iwai, Tomohiro ;

Terao, Jun ;

Tsuji, Yasushi .

CHEMICAL COMMUNICATIONS, 2012, 48 (64) :8012-8014

[8] Palladium Catalyzed Carbonylative Heck Reaction Affording Monoprotected 1,3-Ketoaldehydes [J].

Gogsig, Thomas M. ;

Nielsen, Dennis U. ;

Lindhardt, Anders T. ;

Skrydstrup, Troels .

ORGANIC LETTERS, 2012, 14 (10) :2536-2539

[9] Ex Situ Generation of Stoichiometric and Substoichiometric 12CO and 13CO and Its Efficient Incorporation in Palladium Catalyzed Aminocarbonylations [J].

Hermange, Philippe ;

Lindhardt, Anders T. ;

Taaning, Rolf H. ;

Bjerglund, Klaus ;

Lupp, Daniel ;

Skrydstrup, Troels .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (15) :6061-6071

[10] Palladium-Catalyzed Hydroesterification of Alkynes Employing Aryl Formates without the Use of External Carbon Monoxide [J].

Katafuchi, Yuko ;

Fujihara, Tetsuaki ;

Iwai, Tomohiro ;

Terao, Jun ;

Tsuji, Yasushi .

ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (2-3) :475-482