Recent Progress in Benzylic C(sp3)-H Functionalization of Toluene and Its Derivatives

被引：5

作者：

Cai Chenyi ^{[1
]}

Zou Dong ^{[1
]}

机构：

[1] Zhejiang Univ, Sir Run Run Shaw Hosp, Coll Med, Dept Pharm, Hangzhou 310013, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 42卷 / 06期

关键词：

toluene; C(sp(3))-H bond activation; inert; selective catalysis; C-X bonds formation; C-H BONDS; CATALYZED OXIDATIVE ESTERIFICATION; CARBOXYLIC-ACID DERIVATIVES; METAL-FREE; EFFICIENT SYNTHESIS; ACTIVATION; AMINATION; SILYLATION; ARYLATION; SP(3);

D O I：

10.6023/cjoc202201027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Toluene derivatives are alkyl aromatic hydrocarbons derived from oil and natural gas and are among the cheapest and most readily available materials for the chemical industry. C-H functionalization is important for the synthesis of various bioactive substances, and inert benzylic hydrocarbon bond activation has long been a big challenge in this field due to the high hydrocarbon bond energy. Therefore, the development of simple and efficient methods for C-C and C-X bonds formation has been demonstrated as one of the hot topics by activating the benzylic C(sp(3))-H bonds in recent years. The progress in benzylic C(sp(3))-H functionalization of toluene and its derivatives under different catalytic conditions in the past decade is summarized according to different reaction classifications. The reaction substrate compatibility, mechanism, applications, advantages and limitations in this field are also discussed in detail.

引用

页码：1586 / 1608

页数：23

共 138 条

[1] Carbon tetrachloride free benzylic brominations of methyl aryl halides [J].

Amijs, CHM ;

van Klink, GPM ;

van Koten, G .

GREEN CHEMISTRY, 2003, 5 (04) :470-474

[2] New Si-C bond forming reactions over solid-base catalysts [J].

Baba, T ;

Kato, A ;

Yuasa, H ;

Toriyama, F ;

Handa, H ;

Ono, Y .

CATALYSIS TODAY, 1998, 44 (1-4) :271-276

[3] Metal-free sp3 C-H functionalization: a novel approach for the syntheses of selenide ethers and thioesters from methyl arenes [J].

Badsara, Satpal Singh ;

Liu, Yi-Chen ;

Hsieh, Ping-An ;

Zeng, Jing-Wen ;

Lu, Shao-Yi ;

Liu, Yi-Wei ;

Lee, Chin-Fa .

CHEMICAL COMMUNICATIONS, 2014, 50 (77) :11374-11377

[4] Transition metal-catalyzed arylation of unactivated C(sp3)-H bonds [J].

Baudoin, Olivier .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :4902-4911

[5] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[6] Additive effects on palladium-catalyzed deprotonative-cross-coupling processes (DCCP) of sp3 C-H bonds in diarylmethanes [J].

Bellomo, Ana ;

Zhang, Jiadi ;

Trongsiriwat, Nisalak ;

Walsh, Patrick J. .

CHEMICAL SCIENCE, 2013, 4 (02) :849-857

[7] Efficient copper-catalyzed benzylic amidation with anhydrous chloramine-T [J].

Bhuyan, Ranjana ;

Nicholas, Kenneth M. .

ORGANIC LETTERS, 2007, 9 (20) :3957-3959

[8] EQUILIBRIUM ACIDITIES IN DIMETHYL-SULFOXIDE SOLUTION [J].

BORDWELL, FG .

ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (12) :456-463

[9] Looking on heterogeneous catalytic systems from different perspectives:: Multitechnique approaches as a new challenge for in situ studies [J].

Brückner, A .

CATALYSIS REVIEWS-SCIENCE AND ENGINEERING, 2003, 45 (01) :97-150

[10] Liquid-phase oxidation of alkylaromatics by a H-atom transfer mechanism with a new heterogeneous CoSBA-15 catalyst [J].

Brutchey, RL ;

Drake, IJ ;

Bell, AT ;

Tilley, TD .

CHEMICAL COMMUNICATIONS, 2005, (29) :3736-3738

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