Title:
METHOD FOR SYNTHESIZING Α-ARYL, HETEROARYL OR ALKENYL-Α,Α-2-FLUORO ALLYL STRUCTURE BY PALLADIUM CATALYSIS
Document Type and Number:
WIPO Patent Application WO/2015/081827
Kind Code:
A1
Abstract:
Disclosed is a method for synthesizing a α-aryl, heteroaryl or alkenyl-α,α-2-fluoro allyl structure by palladium catalysis. Specifically, in the method of the present invention, a compound of formula A and a compound of formula B synthesize a compound of formula C under catalysis of a palladium salt and with existence of an alkali and/or ligand, and the compound definition is seen in the specification. The method has advantages such as being simple in raw material, easy to get, small in catalyst dosage, wide in substrate application range, simple and convenient in operation, and high in reaction efficiency, and the manufactured product is widely applied to aspects such as biological medicines, agricultural chemicals and material sciences.
Inventors:
ZHANG XINGANG (CN)
MIN QIAOQIAO (CN)
MIN QIAOQIAO (CN)
Application Number:
PCT/CN2014/092712
Publication Date:
June 11, 2015
Filing Date:
December 01, 2014
Export Citation:
Assignee:
SHANGHAI INST ORGANIC CHEM (CN)
International Classes:
C07B37/00; C07C17/263; C07C22/08; C07C25/24; C07C29/34; C07C33/48; C07C41/30; C07C43/176; C07C43/225; C07C45/68; C07C47/55; C07C67/343; C07C69/65; C07C69/78; C07C201/12; C07C205/11; C07C319/20; C07C323/09; C07D209/86; C07D307/91; C07D333/76; C07J1/00
Other References:
MIN, QIAOQIAO ET AL.: "Highly Selective gem-Difluoroallylation of Organoborons with Bromodifluoromethylated Alkenes Catalyzed by Palladium", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 136, no. 4, 7 January 2014 (2014-01-07), pages 1230 - 1233
YANG GAOSHENG ET AL.: "Palladium Catalyzed Cross-coupling Reaction of Organoboronic Acids with beta-(perfuoroalkyl)ethyl Iodides", JOURNAL OF FLUORINE CHEMISTRY, vol. 98, no. 2, 1 September 1999 (1999-09-01), pages 159 - 161
ASHWOOD, M.S. ET AL.: "Copper-mediated Reaction of 2-halopyridines with Ethyl Bromodifluoroacetate", TETRAHEDRON LETTERS, vol. 43, no. 50, 9 December 2002 (2002-12-09), pages 9271 - 9273, XP004391950, DOI: doi:10.1016/S0040-4039(02)02276-1
SCHWAEBE, M.K. ET AL.: "Nickel(0)-catalyzed Coupling of Vinylzirconiums to a-bromod-a, a-difluoro Esters. Convenient Generation of a Functionalized Allyldifluoro Moiety", TETRAHEDRON LETTERS, vol. 41, no. 6, 5 February 2000 (2000-02-05), pages 791 - 794, XP004188492, DOI: doi:10.1016/S0040-4039(99)02212-1
BELHOMME, M.C. ET AL.: "Copper Catalyzed beta-Ditluoroacetylation of Dihydropyrans and Glycals by Means of Direct C-H Functionalization", ORGANIC LETTERS, vol. 15, no. 13., 21 June 2013 (2013-06-21), pages 3428 - 3431
FENG, ZHANG ET AL.: "Copper Catalyzed Cross-Coupling of Iodobenzoates with Bromozinc-difluorophosphonate", ORGANIC LETTERS, vol. 14, no. 07, 21 March 2012 (2012-03-21), pages 1938 - 1941
DENG, XIANGJUN: "the Synthesis of Gem-Difluoromethylenated Analogues of Natural Products", SCIENCE -ENGINEERING (A), CHINA MASTER'S THESES FULL-TEXT DATABASE, 15 March 2012 (2012-03-15), pages B014 - 68
XIE, YANGFEN: "Synthesis of Fluorine-Containing Fostriecin", SCIENCE -ENGINEERING (A), CHINA MASTER'S THESES FULL-TEXT DATABASE, 15 July 2008 (2008-07-15), pages B016 - 79
YANG GAOSHENG ET AL.: "Palladium Catalyzed Cross-coupling Reaction of Organoboronic Acids with beta-(perfuoroalkyl)ethyl Iodides", JOURNAL OF FLUORINE CHEMISTRY, vol. 98, no. 2, 1 September 1999 (1999-09-01), pages 159 - 161
ASHWOOD, M.S. ET AL.: "Copper-mediated Reaction of 2-halopyridines with Ethyl Bromodifluoroacetate", TETRAHEDRON LETTERS, vol. 43, no. 50, 9 December 2002 (2002-12-09), pages 9271 - 9273, XP004391950, DOI: doi:10.1016/S0040-4039(02)02276-1
SCHWAEBE, M.K. ET AL.: "Nickel(0)-catalyzed Coupling of Vinylzirconiums to a-bromod-a, a-difluoro Esters. Convenient Generation of a Functionalized Allyldifluoro Moiety", TETRAHEDRON LETTERS, vol. 41, no. 6, 5 February 2000 (2000-02-05), pages 791 - 794, XP004188492, DOI: doi:10.1016/S0040-4039(99)02212-1
BELHOMME, M.C. ET AL.: "Copper Catalyzed beta-Ditluoroacetylation of Dihydropyrans and Glycals by Means of Direct C-H Functionalization", ORGANIC LETTERS, vol. 15, no. 13., 21 June 2013 (2013-06-21), pages 3428 - 3431
FENG, ZHANG ET AL.: "Copper Catalyzed Cross-Coupling of Iodobenzoates with Bromozinc-difluorophosphonate", ORGANIC LETTERS, vol. 14, no. 07, 21 March 2012 (2012-03-21), pages 1938 - 1941
DENG, XIANGJUN: "the Synthesis of Gem-Difluoromethylenated Analogues of Natural Products", SCIENCE -ENGINEERING (A), CHINA MASTER'S THESES FULL-TEXT DATABASE, 15 March 2012 (2012-03-15), pages B014 - 68
XIE, YANGFEN: "Synthesis of Fluorine-Containing Fostriecin", SCIENCE -ENGINEERING (A), CHINA MASTER'S THESES FULL-TEXT DATABASE, 15 July 2008 (2008-07-15), pages B016 - 79
Attorney, Agent or Firm:
XU & PARTNERS, LLC. (CN)
上海一平知识产权代理有限公司 (CN)
上海一平知识产权代理有限公司 (CN)
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