Title:
METHOD FOR SYNTHESIZING ALKENYL BORATE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2021/036515
Kind Code:
A1
Abstract:
Provided is a method for synthesizing an alkenyl borate compound, the method comprising: dissolving an alkene compound and a borane compound in a solvent to obtain a mixed solution; adding a zirconium catalyst to the mixed solution; in a protective atmosphere, reacting at 0-150°C for 5 min-8 h to obtain a suspension; and separating the suspension to obtain an alkenyl borate compound; the ratio of the amount of the alkene compound, the borane compound and the zirconium catalyst in the substance is 1:(1-2):(0.01-0.20). In the present invention, the zirconium catalyst is used to react with the borane compound to generate a zirconium boron species and release hydrogen, and then the alkene compound and the zirconium boron species generate an alkyl zirconium species, which then undergoes β-H elimination to form an alkenyl borate compound. Thus, the addition of an additional hydrogen acceptor can be avoided. The results of the examples show that the preparation method of the present invention can synthesize an alkenyl borate compound from an alkene without adding an additional hydrogen acceptor.
Inventors:
WU LIPENG (CN)
SHI XIAONAN (CN)
SHI XIAONAN (CN)
Application Number:
PCT/CN2020/100550
Publication Date:
March 04, 2021
Filing Date:
July 07, 2020
Export Citation:
Assignee:
LANZHOU INST CHEMICAL PHYSICS CAS (CN)
SUZHOU RES INSTITUTE OF LANZHOU INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES (CN)
SUZHOU RES INSTITUTE OF LANZHOU INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES (CN)
International Classes:
C07F5/02; C07F17/02
Foreign References:
| CN110483561A | 2019-11-22 | |||
| CN110407863A | 2019-11-05 |
Other References:
XIAONAN SHI ,SIDA LI , LIPENG WU: "H2-Acceptorless Dehydrogenative Boration and Transfer Boration of Alkenes Enabled by Zirconium Catalyst", ANGEWANDTE CHEMIE, vol. 131, no. 45, 30 September 2019 (2019-09-30), pages 16313 - 16317, XP055786313, ISSN: 0044-8249, DOI: 10.1002/ange.201908931
CHAO WANG, CAIZHI WU, SHAOZHONG GE: "Iron-Catalyzed E-Selective Dehydrogenative Borylation of Vinylarenes with Pinacolborane", ACS CATALYSIS, vol. 6, no. 11, 7 October 2016 (2016-10-07), pages 7585 - 7589, XP055786318, ISSN: 2155-5435, DOI: 10.1021/acscatal.6b02654
LEI ZHANG; ZIQING ZUO; XUEBING LENG; ZHENG HUANG: "A Cobalt-Catalyzed Alkene Hydroboration with Pinacolborane", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 53, no. 10, 3 March 2014 (2014-03-03), pages 2696 - 2700, XP055440768, ISSN: 1433-7851, DOI: 10.1002/anie.201310096
YAMAMOTO Y; FUJIKAWA R; UMEMOTO T; MIYAURA N: "Iridium-Catalyzed Hydroboration of Alkenes with Pinacolborane", TETRAHEDRON, vol. 60, no. 47, 15 November 2004 (2004-11-15), pages 10695 - 10700, XP004603150, ISSN: 0040-4020, DOI: 10.1016/j.tet.2004.09.014
WANG Y D; KIMBALL G; PRASHAD A S; WANG Y: "Zr-Mediated Hydroboration: Stereoselective Synthesis of Vinyl Boronic Esters", TETRAHEDRON LETTERS, vol. 46, no. 50, 12 December 2005 (2005-12-12), pages 8777 - 8780, XP025385352, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2005.10.031
MKHALID IBRAHEEM I A , COAPES R. BENJAMIN, EDES S. NATASHA, COVENTRY DAVID N., SOUZA FABIO E. S., THOMAS RHODRI LL., HALL JONATHAN: "Rhodium Catalysed Dehydrogenative Borylation of Alkenes: Vinylboronates via C H Activation", DALTON TRANSACTIONS, no. 8, 20 December 2007 (2007-12-20), pages 1055 - 1064, XP055786323, ISSN: 1477-9234, DOI: 10.1039/B715584K
CHAO WANG, CAIZHI WU, SHAOZHONG GE: "Iron-Catalyzed E-Selective Dehydrogenative Borylation of Vinylarenes with Pinacolborane", ACS CATALYSIS, vol. 6, no. 11, 7 October 2016 (2016-10-07), pages 7585 - 7589, XP055786318, ISSN: 2155-5435, DOI: 10.1021/acscatal.6b02654
LEI ZHANG; ZIQING ZUO; XUEBING LENG; ZHENG HUANG: "A Cobalt-Catalyzed Alkene Hydroboration with Pinacolborane", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 53, no. 10, 3 March 2014 (2014-03-03), pages 2696 - 2700, XP055440768, ISSN: 1433-7851, DOI: 10.1002/anie.201310096
YAMAMOTO Y; FUJIKAWA R; UMEMOTO T; MIYAURA N: "Iridium-Catalyzed Hydroboration of Alkenes with Pinacolborane", TETRAHEDRON, vol. 60, no. 47, 15 November 2004 (2004-11-15), pages 10695 - 10700, XP004603150, ISSN: 0040-4020, DOI: 10.1016/j.tet.2004.09.014
WANG Y D; KIMBALL G; PRASHAD A S; WANG Y: "Zr-Mediated Hydroboration: Stereoselective Synthesis of Vinyl Boronic Esters", TETRAHEDRON LETTERS, vol. 46, no. 50, 12 December 2005 (2005-12-12), pages 8777 - 8780, XP025385352, ISSN: 0040-4039, DOI: 10.1016/j.tetlet.2005.10.031
MKHALID IBRAHEEM I A , COAPES R. BENJAMIN, EDES S. NATASHA, COVENTRY DAVID N., SOUZA FABIO E. S., THOMAS RHODRI LL., HALL JONATHAN: "Rhodium Catalysed Dehydrogenative Borylation of Alkenes: Vinylboronates via C H Activation", DALTON TRANSACTIONS, no. 8, 20 December 2007 (2007-12-20), pages 1055 - 1064, XP055786323, ISSN: 1477-9234, DOI: 10.1039/B715584K
Attorney, Agent or Firm:
BEIJING GAOWO LAW FIRM (CN)
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