Transition-metal-catalyzed C-H bond activation as a sustainable strategy for the synthesis of fluorinated molecules: an overview

被引：13

作者：

Monsigny, Louis ^{[1
]}

Doche, Floriane ^{[1
]}

Besset, Tatiana ^{[1
]}

机构：

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

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 19卷

基金：

欧洲研究理事会;

关键词：

C-H bond activation; emergent fluorinated groups; homogeneous catalysis; organofluorine chemistry; palladium; synthetic method; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; TRANSIENT DIRECTING GROUPS; ELECTROPHILIC TRIFLUOROMETHYLTHIOLATION; UNACTIVATED C(SP(3))-H; C(SP(2))-H BONDS; MEDIATED TRIFLUOROMETHYLATION; EFFICIENT SYNTHESIS; FUNCTIONALIZATION; ARYL; ALKOXYLATION;

D O I：

10.3762/bjoc.19.35

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The last decade has witnessed the emergence of innovative synthetic tools for the synthesis of fluorinated molecules. Among these approaches, the transition-metal-catalyzed functionalization of various scaffolds with a panel of fluorinated groups (XRF, X = S, Se, O) offered straightforward access to high value-added compounds. This review will highlight the main advances made in the field with the transition-metal-catalyzed functionalization of C(sp2) and C(sp3) centers with SCF3, SeCF3, or OCH2CF3 groups among others, by C-H bond activation. The scope and limitations of these transformations are discussed in this review.

引用

页码：448 / 473

页数：26

共 211 条

[91] Introduction of Fluorine and Fluorine-Containing Functional Groups [J].

Liang, Theresa ;

Neumann, Constanze N. ;

Ritter, Tobias .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (32) :8214-8264

[92] Recent advances in C-H fluorination [J].

Lin, Aijun ;

Huehls, C. Bryan ;

Yang, Jiong .

ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (04) :434-438

[93] Luciferase-induced photoreductive uncaging of small-molecule effectors [J].

Lindberg, Eric ;

Angerani, Simona ;

Anzola, Marcello ;

Winssinger, Nicolas .

NATURE COMMUNICATIONS, 2018, 9

[94] Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds [J].

Liu, Bin ;

Romine, Andrew M. ;

Rubel, Camille Z. ;

Engle, Keary M. ;

Shi, Bing-Feng .

CHEMICAL REVIEWS, 2021, 121 (24) :14957-15074

[95] Transition-metal-catalyzed etherification of unactivated C-H bonds [J].

Liu, Bin ;

Shi, Bing-Feng .

TETRAHEDRON LETTERS, 2015, 56 (01) :15-22

[96] Direct Trifluoromethylation of the CH Bond [J].

Liu, Hui ;

Gu, Zhenhua ;

Jiang, Xuefeng .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (04) :617-626

[97] Direct Dehydroxytrifluoromethylthiolation of Alcohols Using Silver(I) Trifluoromethanethiolate and Tetra-n-butylammonium Iodide [J].

Liu, Jian-Bo ;

Xu, Xiu-Hua ;

Chen, Zeng-Hao ;

Qing, Feng-Ling .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) :897-900

[98] Enantioselective Trifluoromethylthiolating Lactonization Catalyzed by an Indane-Based Chiral Sulfide [J].

Liu, Xiang ;

An, Rui ;

Zhang, Xuelin ;

Luo, Jie ;

Zhao, Xiaodan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (19) :5846-5850

[99] (Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed Direct Trifluoromethylthiolation of Arenes via C-H Activation [J].

Liu, Xu-Ge ;

Li, Qingjiang ;

Wang, Honggen .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (11) :1942-1946

[100] Pd(OAc)2-catalyzed regioselective aromatic C-H bond fluorination [J].

Lou, Shao-Jie ;

Xu, Dan-Qian ;

Xia, Ai-Bao ;

Wang, Yi-Feng ;

Liu, Yun-Kui ;

Du, Xiao-Hua ;

Xu, Zhen-Yuan .

CHEMICAL COMMUNICATIONS, 2013, 49 (55) :6218-6220

← 5 6 7 8 9 10 11 12 13 14 →