Photocatalytic hydroacylation of trifluoromethyl alkenes

被引：65

作者：

Fan, Pei ^{[1
]}

Zhang, Chang ^{[1
]}

Lan, Yun ^{[1
]}

Lin, Zhiyang ^{[1
]}

Zhang, Linchuan ^{[1
]}

Wang, Chuan ^{[1
]}

机构：

[1] Hefei Univ Sci & Technol China, Dept Chem, Ctr Excellence Mol Synth, Natl Lab Phys Sci Microscale, 96 Jinzhai Rd, Hefei 20237, Anhui, Peoples R China

来源：

CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 84期

基金：

中国国家自然科学基金;

关键词：

NUCLEOPHILIC 5-ENDO-TRIG CYCLIZATION; FUNCTIONALIZED GEM-DIFLUOROALKENES; REGIOSELECTIVE 1,4-TRIFLUOROMETHYLATION; ELECTROPHILIC ALKENES; DECATUNGSTATE ANION; MAGNETIC-RESONANCE; RADICAL REACTIONS; ADDITION-REACTION; ALKYLATION; FLUORINE;

D O I：

10.1039/c9cc07285c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Hydrofunctionalization of trifluoromethyl alkenes is highly challenging, because the nucleophilic addition is oftentimes followed by beta-F elimination in this case. By the use of tetrabutylammonium decatungstate (TBADT) as a hydrogen-atom-transfer (HAT) photocatalyst for acyl C-H activation, we successfully avoid the beta-F elimination in the hydroacylation of trifluoromethyl alkenes with aldehydes. This light (390 nm) promoted reaction provides a facile and efficient access to various beta-CF3 ketones in complete regiocontrol with high functionality tolerance and 100% atom economy.

引用

页码：12691 / 12694

页数：4

共 97 条

[1]

Begue J.-P., 1996, J CHEM SOC P1, V1, P1409

[2] The chemistry of trifluoromethyl imines and related acetals derived from fluoral [J].

Bégué, JP ;

Bonnet-Delpon, D ;

Crousse, B ;

Legros, J .

CHEMICAL SOCIETY REVIEWS, 2005, 34 (07) :562-572

[3] A CONCISE SYNTHESIS OF FUNCTIONALIZED GEM-DIFLUOROALKENES VIA THE ADDITION OF ORGANOLITHIUM REAGENTS TO ALPHA-TRIFLUOROMETHYLSTYRENE [J].

BEGUE, JP ;

BONNETDELPON, D ;

ROCK, MH .

TETRAHEDRON LETTERS, 1995, 36 (28) :5003-5006

[4] ADDITION-REACTION OF 3,3,3-TRIFLUOROPROPENE TO TETRAHYDROFURAN - TELOMERIC GROWTH VIA FREE-RADICAL REARRANGEMENTS [J].

BERGSTROM, DE ;

NG, MW ;

WONG, JJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (04) :741-745

[5] Electrophilic Trifluoromethylation by Use of Hypervalent Iodine Reagents [J].

Charpentier, Julie ;

Frueh, Natalja ;

Togni, Antonio .

CHEMICAL REVIEWS, 2015, 115 (02) :650-682

[6] COPPER ELECTRON-TRANSFER INDUCED TRIFLUOROMETHYLATION WITH METHYL FLUOROSULPHONYLDIFLUOROACETATE [J].

CHEN, QY ;

YANG, GY ;

WU, SW .

JOURNAL OF FLUORINE CHEMISTRY, 1991, 55 (03) :291-298

[7] METHYL FLUOROSULFONYLDIFLUOROACETATE - A NEW TRIFLUOROMETHYLATING AGENT [J].

CHEN, QY ;

WU, SW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) :705-706

[8] 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

[9] Cu-Catalyzed tertiary alkylation of α-(trifluoromethyl) styrenes with tertiary alkylmagnesium reagents [J].

Dai, Wenpeng ;

Lin, Yingyin ;

Wan, Yan ;

Cao, Song .

ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (01) :55-58

[10] Fluorinated high-performance polymers: Poly(arylene ether)s and aromatic polyimides containing trifluoromethyl groups [J].

Dhara, Mahua G. ;

Banerjee, Susanta .

PROGRESS IN POLYMER SCIENCE, 2010, 35 (08) :1022-1077

← 1 2 3 4 5 6 7 8 9 10 →