Title:
3, 3-DIFLUOROALLYLIC ONIUM SALT COMPOUND AND PREPARATION METHOD THEREFOR AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2023/030279
Kind Code:
A1
Abstract:
Provided are a 3, 3-difluoroallylic onium salt as represented by formula (C), and a preparation method of the substance. Cheap industrial raw materials are used to prepare the important fluorine-containing reagent, which can be used as an α,α-gem-difluoroallylation reagent. The present invention provides a more universal and cheap new method for α,α-gem-difluoroallylation, and is high in efficiency and good in application prospects.
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Inventors:
ZHANG XINGANG (CN)
MIN QIAOQIAO (CN)
FENG XIAOTIAN (CN)
GAO XING (CN)
REN JINXIU (CN)
MIN QIAOQIAO (CN)
FENG XIAOTIAN (CN)
GAO XING (CN)
REN JINXIU (CN)
Application Number:
PCT/CN2022/115642
Publication Date:
March 09, 2023
Filing Date:
August 29, 2022
Export Citation:
Assignee:
SHANGHAI INSITITUTE OF ORGANIC CHEMISTRY CHINESE ACAD OF SCIENCES (CN)
International Classes:
C07C381/12; C07C17/263; C07C21/18; C07C22/08; C07C25/24; C07C69/65; C07C69/76; C07C69/92; C07C253/30; C07C255/50; C07C319/20; C07C323/09; C07D207/16; C07D209/08; C07D327/06; C07F7/08; C07F7/18; C07F9/40
Foreign References:
| CN106349134A | 2017-01-25 | |||
| US3426046A | 1969-02-04 | |||
| CN115260069A | 2022-11-01 |
Other References:
MIN QIAO-QIAO, YIN ZENGSHENG, FENG ZHANG, GUO WEN-HAO, ZHANG XINGANG: "Highly Selective gem -Difluoroallylation of Organoborons with Bromodifluoromethylated Alkenes Catalyzed by Palladium", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 136, no. 4, 29 January 2014 (2014-01-29), pages 1230 - 1233, XP093043181, ISSN: 0002-7863, DOI: 10.1021/ja4114825
YE FEI, GE YAO, SPANNENBERG ANKE, NEUMANN HELFRIED, XU LI-WEN, BELLER MATTHIAS: "3,3-Difluoroallyl ammonium salts: highly versatile, stable and selective gem-difluoroallylation reagents", NATURE COMMUNICATIONS, vol. 12, no. 1, XP093043184, DOI: 10.1038/s41467-021-23504-2
GU, WENXIANG: "Synthesis of a new sulfonium salt", HUAXUE SHIJI - CHEMICAL REAGENTS, BEIJING : HUAXUE HUAXUE SHIJI KEJI QINGBAO ZHONGXINZHAN, CN, vol. 14, no. 6, 31 December 1992 (1992-12-31), CN , pages 364, 376, XP009544255, ISSN: 0258-3283, DOI: 10.13822/j.cnki.hxsj.1992.06.016
ZHANG, XIAOMEI: "Synthesis and Reactions of Dimethyl-3,3-dichloro-2-propenylsulfonium Chloride", ACTA CHIMICA SINICA, vol. 48, no. 3, 1 January 1990 (1990-01-01), pages 273 - 282, XP093043193
LEO A. PAQUETTE: "Encyclopedia of reagents for organic synthesis; Vol. 7 : Sod - Trim", WILEY , Chichester , ISBN: 978-0-470-84289-8, article CHAMBLEE THERESA S.: "3-Bromo-1,1-dichloro-1-propene", XP093043196, DOI: 10.1002/047084289X.rb287m
OSUKA OSUKA ATSUHIRO ATSUHIRO, SUZUKI HITOMI: "Dialkyltelluronium allylide as a novel reagent for synthesis of α,β-unsaturated epoxides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 24, no. 46, 1 January 1983 (1983-01-01), Amsterdam , NL , pages 5109 - 5112, XP093043198, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)94054-1
XUN HAN, YE, SUN LONGWU B, XIULI: "Cyclization Reactions for the Stereoselective Synthesis of Small Ring Compounds via Selenonium and Telluronium Ylides", CHINESE JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 3, 1 January 2009 (2009-01-01), pages 306 - 320, XP093043201
YE FEI, GE YAO, SPANNENBERG ANKE, NEUMANN HELFRIED, XU LI-WEN, BELLER MATTHIAS: "3,3-Difluoroallyl ammonium salts: highly versatile, stable and selective gem-difluoroallylation reagents", NATURE COMMUNICATIONS, vol. 12, no. 1, XP093043184, DOI: 10.1038/s41467-021-23504-2
GU, WENXIANG: "Synthesis of a new sulfonium salt", HUAXUE SHIJI - CHEMICAL REAGENTS, BEIJING : HUAXUE HUAXUE SHIJI KEJI QINGBAO ZHONGXINZHAN, CN, vol. 14, no. 6, 31 December 1992 (1992-12-31), CN , pages 364, 376, XP009544255, ISSN: 0258-3283, DOI: 10.13822/j.cnki.hxsj.1992.06.016
ZHANG, XIAOMEI: "Synthesis and Reactions of Dimethyl-3,3-dichloro-2-propenylsulfonium Chloride", ACTA CHIMICA SINICA, vol. 48, no. 3, 1 January 1990 (1990-01-01), pages 273 - 282, XP093043193
LEO A. PAQUETTE: "Encyclopedia of reagents for organic synthesis; Vol. 7 : Sod - Trim", WILEY , Chichester , ISBN: 978-0-470-84289-8, article CHAMBLEE THERESA S.: "3-Bromo-1,1-dichloro-1-propene", XP093043196, DOI: 10.1002/047084289X.rb287m
OSUKA OSUKA ATSUHIRO ATSUHIRO, SUZUKI HITOMI: "Dialkyltelluronium allylide as a novel reagent for synthesis of α,β-unsaturated epoxides", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 24, no. 46, 1 January 1983 (1983-01-01), Amsterdam , NL , pages 5109 - 5112, XP093043198, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(00)94054-1
XUN HAN, YE, SUN LONGWU B, XIULI: "Cyclization Reactions for the Stereoselective Synthesis of Small Ring Compounds via Selenonium and Telluronium Ylides", CHINESE JOURNAL OF ORGANIC CHEMISTRY, vol. 29, no. 3, 1 January 2009 (2009-01-01), pages 306 - 320, XP093043201
Attorney, Agent or Firm:
SHANGHAI BESHINING LAW OFFICE (CN)
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