Dual Photoredox/Copper Catalyzed Fluoroalkylative Alkene Difunctionalization

被引：12

作者：

Kostromitin, Vladislav S. ^{[1
,2
]}

Levin, Vitalij V. ^{[1
]}

Dilman, Alexander D. ^{[1
]}

机构：

[1] N D Zelinsky Inst Organ Chem, Moscow 119991, Russia

[2] Lomonosov Moscow State Univ, Dept Chem, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 09期

基金：

俄罗斯科学基金会;

关键词：

SHINING LIGHT; RADICALS; COPPER;

D O I：

10.1021/acs.joc.3c00448

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A method for performing radical difunctionalization of alkenes using fluorinated halides and a nucleophilic component (thiolate and iodide anions) is described. These nucleophilic fragments serve as redox active groups for performing subsequent transformations. The difunctionalization reaction involves photoredox generation of fluorinated radicals, their addition to the double bond followed by copper promoted C-S or C-I bond formation. The primary products can be further coupled with silyl enol ethers, alpha- (trifluoromethyl)styrenes, and trimethylsilyl cyanide affording a variety of fluorinated compounds.

引用

页码：6252 / 6262

页数：11

共 51 条

[1] Developments in Photoredox/Nickel Dual-Catalyzed 1,2-Difunctionalizations [J].

Badir, Shorouk O. ;

Molandert, Gary A. .

CHEM, 2020, 6 (06) :1327-1339

[2] Radical-Mediated Difunctionalization of Styrenes [J].

Bao, Xiazhen ;

Li, Jun ;

Jiang, Wei ;

Huo, Congde .

SYNTHESIS-STUTTGART, 2019, 51 (24) :4507-4530

[3] Radical Fluoroalkylation Reactions [J].

Barata-Vallejo, Sebastian ;

Victoria Cooke, Maria ;

Postigo, Al .

ACS CATALYSIS, 2018, 8 (08) :7287-7307

[4] CYCLIZATION OF 3-ALLYLHEX-5-ENYL RADICAL - MECHANISM, AND IMPLICATIONS CONCERNING STRUCTURES OF CYCLOPOLYMERS [J].

BECKWITH, ALJ ;

MOAD, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (15) :1726-1733

[5]

BESTMANN HJ, 1982, LIEBIGS ANN CHEM, V115, P828

[6] Olefin difunctionalizations via visible light photocatalysis [J].

Cao, Min-Yi ;

Ren, Xiang ;

Lu, Zhan .

TETRAHEDRON LETTERS, 2015, 56 (24) :3732-3742

[7] Z-Selective Alkene Isomerization by High-Spin Cobalt(II) Complexes [J].

Chen, Chi ;

Dugan, Thomas R. ;

Brennessel, William W. ;

Weix, Daniel J. ;

Holland, Patrick L. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :945-955

[8] Recent developments in the difunctionalization of alkenes with C-N bond formation [J].

Chen, Xiang ;

Xiao, Fang ;

He, Wei-Min .

ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (18) :5206-5228

[9] Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins [J].

Crossley, Steven W. M. ;

Obradors, Carla ;

Martinez, Ruben M. ;

Shenvi, Ryan A. .

CHEMICAL REVIEWS, 2016, 116 (15) :8912-9000

[10]

Dagousset G, 2017, PROGR FLUOR SCI SER, V3, P389, DOI 10.1016/B978-0-12-803740-9.00014-7

← 1 2 3 4 5 6 →