Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes

被引：38

作者：

Poutrel, Pauline ^{[1
]}

Pannecoucke, Xavier ^{[1
]}

Jubault, Philippe ^{[1
]}

Poisson, Thomas ^{[1
,2
]}

机构：

[1] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA,UMR 6014, F-76000 Rouen, France

[2] Inst Univ France, F-75231 Paris, France

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

关键词：

PALLADIUM-CATALYZED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; GEM-DIFLUOROALKENES; FLUORINE; OLEFINATION; ANALOGS; 3,3-DIFLUOROPROPENES; CYCLOPROPANATION; DERIVATIVES; INHIBITORS;

D O I：

10.1021/acs.orglett.0c01701

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report the hydrodefluorination reaction of trifluoromethylated alkenes to access terminal monofluoroalkenes. The use of LiAlH4 allowed the stereoselective synthesis of the terminal monofluoroalkenes in good to excellent yields with good to excellent diastereoselectivities. Mechanistic studies suggested a hydroalumination reaction followed by a stereoselective fluoride elimination.

引用

页码：4858 / 4863

页数：6

共 68 条

[1] Selective Copper Complex-Catalyzed Hydrodefluorination of Fluoroalkenes and Allyl Fluorides: A Tale of Two Mechanisms [J].

Andrella, Nicholas O. ;

Xu, Nancy ;

Gabidullin, Bulat M. ;

Ehm, Christian ;

Baker, R. Tom .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (29) :11506-11521

[2] Synthesis and antibacterial activity of 1-(2-fluorovinyl)-7-substituted-4-quinolone-3-carboxylic acid derivatives, conformationally restricted analogues of fleroxacin [J].

Asahina, Y ;

Iwase, K ;

Iinuma, F ;

Hosaka, M ;

Ishizaki, T .

JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (09) :3194-3202

[3] Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers [J].

Belhomme, Marie-Charlotte ;

Besset, Tatiana ;

Poisson, Thomas ;

Pannecoucke, Xavier .

CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (37) :12836-12865

[4] SN2′ Reaction of Allylic Difluorides with Lithium Amides and Thiolates [J].

Bergeron, Maxime ;

Guyader, David ;

Paquin, Jean-Francois .

ORGANIC LETTERS, 2012, 14 (23) :5888-5891

[5] The Use of Fluoride as a Leaving Group: SN2' Displacement of a C?F Bond on 3,3-Difluoropropenes with Organolithium Reagents To Give Direct Access to Monofluoroalkenes [J].

Bergeron, Maxime ;

Johnson, Thomas ;

Paquin, Jean-Francois .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (47) :11112-11116

[6] New entries toward the synthesis of OCF3-containing molecules [J].

Besset, Tatiana ;

Jubault, Philippe ;

Pannecoucke, Xavier ;

Poisson, Thomas .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (08) :1004-1010

[7] Catalytic Enantioselective Synthesis of Highly Functionalized Difluoromethylated Cyclopropanes [J].

Bos, Maxence ;

Huang, Wei-Sheng ;

Poisson, Thomas ;

Pannecoucke, Xavier ;

Charette, Andre B. ;

Jubault, Philippe .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) :13319-13323

[8] ALPHA-FLUOROMETHYL-N-METHYL-PHENYLSULPHOXIMINE - A NEW FLUOROMETHYLENATION REAGENT [J].

BOYS, ML ;

COLLINGTON, EW ;

FINCH, H ;

SWANSON, S ;

WHITEHEAD, JF .

TETRAHEDRON LETTERS, 1988, 29 (27) :3365-3368

[9] Monofluorination of Organic Compounds: 10 Years of Innovation [J].

Champagne, Pier Alexandre ;

Desroches, Justine ;

Hamel, Jean-Denys ;

Vandamme, Mathilde ;

Paquin, Jean-Francois .

CHEMICAL REVIEWS, 2015, 115 (17) :9073-9174

[10] Inhibition of hepatitis C virus NS5A by fluoro-olefin based γ-turn mimetics [J].

Chang, Wonsuk ;

Mosley, Ralph T. ;

Bansal, Shalini ;

Keilman, Meg ;

Lam, Angela M. ;

Furman, Phillip A. ;

Otto, Michael J. ;

Sofia, Michael J. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (08) :2938-2942

← 1 2 3 4 5 6 7 →