Light-Promoted Allylation of Iododifluoromethylated Alcohols

被引:8
作者
Panferova, Liubov I. [1 ]
Struchkova, Marina I. [1 ]
Dilman, Alexander D. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Leninsky Prosp 47, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
Organofluorine compounds; Silicon; Radicals; Atom transfer; Photocatalysis; TRANSFER RADICAL ADDITIONS; PHOTOREDOX CATALYSIS; TRIFLUOROMETHYLATION; FLUORINE; SILICON;
D O I
10.1002/ejoc.201800543
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the synthesis of ,-difluorinated alcohols by the formal substitution of iodine in the iododifluoromethyl fragment by the allyl group is described. The reaction involves silylation of the starting alcohols with allyl(chloro)dimethylsilane followed by an light-promoted atom transfer process. The C,C-bond-forming event proceeds through 7-endo-trig radical cyclization.
引用
收藏
页码:3834 / 3836
页数:3
相关论文
共 41 条
[1]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[2]  
Arceo E., 2014, ANGEW CHEM, V126, P12260
[3]   Photo-Organocatalysis of Atom-Transfer Radical Additions to Alkenes [J].
Arceo, Elena ;
Montroni, Elisa ;
Melchiorre, Paolo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (45) :12064-12068
[4]   Cyclization of methyl-substituted 6-heptenyl radicals [J].
Bailey, WF ;
Longstaff, SC .
ORGANIC LETTERS, 2001, 3 (14) :2217-2219
[5]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF ALKENYL RADICAL RING-CLOSURE - A THEORETICAL-STUDY [J].
BECKWITH, ALJ ;
SCHIESSER, CH .
TETRAHEDRON, 1985, 41 (19) :3925-3941
[6]   Benzophenone vs. Copper/Benzophenone in Light-Promoted Atom Transfer Radical Additions (ATRAs): Highly Effective Iodoperfluoroalkylation of Alkenes/Alkynes and Mechanistic Studies [J].
Beniazza, Redouane ;
Atkinson, Rachel ;
Absalon, Christelle ;
Castet, Frederic ;
Denisov, Sergey A. ;
McClenaghan, Nathan D. ;
Lastecoueres, Dominique ;
Vincent, Jean-Marc .
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (18) :2949-2961
[7]   MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID [J].
BLACKBURN, GM ;
ENGLAND, DA ;
KOLKMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :930-932
[8]   Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].
Charpentier, Julie ;
Frueh, Natalja ;
Togni, Antonio .
CHEMICAL REVIEWS, 2015, 115 (02) :650-682
[9]   Controlled Fluoroalkylation Reactions by Visible-Light Photoredox Catalysis [J].
Chatterjee, Tanmay ;
Iqbal, Naeem ;
You, Youngmin ;
Cho, Eun Jin .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2284-2294
[10]   Oxidative Trifluoromethylation and Trifluoromethylthiolation Reactions Using (Trifluoromethyl)trimethylsilane as a Nucleophilic CF3 Source [J].
Chu, Lingling ;
Qing, Feng-Ling .
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (05) :1513-1522