Palladium-Catalyzed Reductive Carbonylation of Aryl Halides with N-Formylsaccharin as a CO Source

被引：198

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：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 33期

关键词：

aldehydes; arenes; carbonylation; palladium; synthetic methods; ATMOSPHERIC-PRESSURE; VINYL HALIDES; EFFICIENT; BROMIDES; FORMATE; HYDROXYCARBONYLATION; FORMYLATION; ALKOXYCARBONYLATION; DECARBONYLATION; CHLORIDES;

D O I：

10.1002/anie.201303926

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Easy peasy: The title reaction employs N-formylsaccharin, which is an easily accessible crystalline compound, as an effective CO source. The reactions proceed with a small excess of the CO source at moderate temperatures and were successfully applied to a wide range of aryl bromides. DMF=N,N- dimethylformamide, dppb=1,4-bis-(diphenylphosphino)butane. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

收藏

页码：8611 / 8615

页数：5

相关论文

共 38 条

[1] Reductive carbonylation - an efficient and practical catalytic route for the conversion of aryl halides to aldehydes [J].

Ashfield, Laura ;

Barnard, Christopher F. J. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2007, 11 (01) :39-43

[2] Palladium-catalyzed hydroxycarbonylation of aryl and vinyl bromides by mixed acetic formic anhydride [J].

Berger, Philippe ;

Bessmernykh, Alla ;

Caille, Jean-Claude ;

Mignonac, Sylviane .

SYNTHESIS-STUTTGART, 2006, (18) :3106-3110

[3] 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

[4]

Brennfuhrer A., 2009, ANGEW CHEM, V121, P4176

[5] Palladium-catalyzed synthesis of aldehydes from aryl iodides and acetic formic anhydride [J].

Cacchi, S ;

Fabrizi, G ;

Goggiamani, A .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05) :692-694

[6] 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

[7] 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

[8] N-Formylsaccharin: A New Formylating Agent [J].

Cochet, Thomas ;

Bellosta, Veronique ;

Greiner, Alfred ;

Roche, Didier ;

Cossy, Janine .

SYNLETT, 2011, (13) :1920-1922

[9] 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

[10] 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

← 1 2 3 4 →