Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light

被引:155
作者
Liu, Peng [1 ,2 ,3 ]
Liu, Wenbo [1 ,2 ]
Li, Chao-Jun [1 ,2 ]
机构
[1] McGill Univ, Dept Chem, 801 Sherbrooke St W, Montreal, PQ H3A 0B8, Canada
[2] McGill Univ, FQRNT Ctr Green Chem & Catalysis, 801 Sherbrooke St W, Montreal, PQ H3A 0B8, Canada
[3] Wuhan Univ, Hubei Prov Engn & Technol Res Ctr Fluorinated Pha, Key Lab Combinatorial Biosynth & Drug Discovery, Minist Educ,Sch Pharmaceut Sci, Wuhan 430071, Hubei, Peoples R China
基金
加拿大自然科学与工程研究理事会;
关键词
C-H FUNCTIONALIZATION; PROTONATED HETEROAROMATIC BASES; ELECTRON-TRANSFER PROCESSES; ENGINEERING REACTIONS; CRYSTALLINE SOLIDS; RADICAL REACTIONS; NUCLEOPHILIC TRIFLUOROMETHYLATION; PHOTOCHEMICAL GENERATION; NITROGEN HETEROAROMATICS; HOMOLYTIC ALKYLATION;
D O I
10.1021/jacs.7b08685
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Minisci alkylation is useful to functionalize aromatics via alkyl radical addition. Current approaches to prepare alkyl radicals follow either oxidative or reductive pathways from various functional groups. Developing new strategy beyond these traditional methods remains elusive yet highly significant. In this article, we present a redox-neutral and catalyst-free protocol to engender alkyl radicals in the context of trifluoromethylation and general alkylation of arenes. This protocol, via the Norrish type I concept to produce alkyl radicals, accommodates various functional groups and delivers the product in good yields. This method identified a series of compounds as the trifluoromethylation and alkylation reagents assisted by light. It is expected that these compounds can find potential applications in other radical-involved reactions.
引用
收藏
页码:14315 / 14321
页数:7
相关论文
共 137 条
[61]   PHOTOCHEMISTRY OF ALKYL-HALIDES .4. 1-NORBORNYL, 1-NORBORNYLMETHYL, 1-ADAMANTYL AND 2-ADAMANTYL, AND 1-OCTYL BROMIDES AND IODIDES [J].
KROPP, PJ ;
POINDEXTER, GS ;
PIENTA, NJ ;
HAMILTON, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (25) :8135-8144
[62]   PHOTOCHEMISTRY OF ALKYL-HALIDES .1. IONIC VS RADICAL BEHAVIOR [J].
KROPP, PJ ;
JONES, TH ;
POINDEXT.GS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (16) :5420-5421
[63]   PHOTOCHEMISTRY OF ALKYL-HALIDES .9. GEMINAL DIHALIDES [J].
KROPP, PJ ;
PIENTA, NJ .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (12) :2084-2090
[64]   A NEW APPROACH TO THE PHOTOCHEMICAL TRIFLUOROMETHYLATION OF AROMATIC-COMPOUNDS [J].
LAI, CW ;
MALLOUK, TE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (17) :1359-1361
[65]   Nucleophilic trifluoromethylation of aryl halides with methyl trifluoroacetate [J].
Langlois, Bemard R. ;
Roques, Nicolas .
JOURNAL OF FLUORINE CHEMISTRY, 2007, 128 (10) :1318-1325
[66]   TRIFLUOROMETHYLATION OF AROMATIC-COMPOUNDS WITH SODIUM TRIFLUOROMETHANESULFINATE UNDER OXIDATIVE CONDITIONS [J].
LANGLOIS, BR ;
LAURENT, E ;
ROIDOT, N .
TETRAHEDRON LETTERS, 1991, 32 (51) :7525-7528
[67]   Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction [J].
Li, Lu ;
Mu, Xiaoyue ;
Liu, Wenbo ;
Wang, Yichen ;
Mi, Zetian ;
Li, Chao-Jun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (18) :5809-5812
[68]   Transition-metal-free cross-dehydrogenative alkylation of pyridines under neutral conditions [J].
Li, Xin ;
Wang, Hao-Yuan ;
Shi, Zhang-Jie .
NEW JOURNAL OF CHEMISTRY, 2013, 37 (06) :1704-1706
[69]   Simple and Clean Photo-induced Methylation of Heteroarenes with MeOH [J].
Liu, Wenbo ;
Yang, Xiaobo ;
Zhou, Zhong-Zhen ;
Li, Chao-Jun .
CHEM, 2017, 2 (05) :688-702
[70]   Fe-Catalyzed C-C Bond Construction from Olefins via Radicals [J].
Lo, Julian C. ;
Kim, Dongyoung ;
Pan, Chung-Mao ;
Edwards, Jacob T. ;
Yabe, Yuki ;
Gui, Jinghan ;
Qin, Tian ;
Gutierrez, Sara ;
Giacoboni, Jessica ;
Smith, Myles W. ;
Holland, Patrick L. ;
Baran, Phil S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (06) :2484-2503