Nickel-Catalyzed Directed Benzylation of Ortho C-H Bonds in Aromatic Amides through C-H/C-N Cleavage

被引：24

作者：

Li, Jiawei ^{[1
]}

Zheng, Zhaojing ^{[2
]}

Xiao, Tiantian ^{[1
]}

Xu, Peng-Fei ^{[2
]}

Wei, Hao ^{[1
]}

机构：

[1] Northwest Univ, Coll Chem & Mat Sci, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Xian 710127, Shaanxi, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 7卷 / 01期

基金：

中国国家自然科学基金;

关键词：

ammonium salts; benzylation; C-N bond cleavage; cross-coupling; nickel catalysis; UNACTIVATED C(SP(3))-H BONDS; BIDENTATE-CHELATION ASSISTANCE; ARYL GRIGNARD-REAGENTS; FUNCTIONAL MOLECULES; OXIDATIVE ADDITION; COUPLING REACTIONS; DIRECT ARYLATION; AMMONIUM-SALTS; ACTIVATION; ALKYLATION;

D O I：

10.1002/ajoc.201700569

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The cleavage of both sp(2) C-H and C-N bonds by a nickel-catalyzed reaction of aromatic amides containing an 8-aminoquinoline moiety with benzyl ammonium salts is reported. A wide variety of functional groups are tolerated in the reaction. Preliminary mechanistic investigations indicate that the reaction probably proceeds through a Ni-I/Ni-III catalytic pathway. This Ni-catalyzed procedure provides an alternative approach to construct diarylmethane derivatives.

引用

页码：133 / 136

页数：4

共 67 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] The Nickel(II)-Catalyzed Direct Benzylation, Allylation, Alkylation, and Methylation of C-H Bonds in Aromatic Amides Containing an 8-Aminoquinoline Moiety as the Directing Group [J].

Aihara, Yoshinori ;

Wuelbern, Jendrik ;

Chatani, Naoto .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2015, 88 (03) :438-446

[3] Ni(II)-Catalyzed Oxidative Coupling between C(sp2)-H in Benzamides and C(sp3)-H in Toluene Derivatives [J].

Aihara, Yoshinori ;

Tobisu, Mamoru ;

Fukumoto, Yoshiya ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15509-15512

[4] Nickel-Catalyzed Direct Arylation of C(sp3)-H Bonds in Aliphatic Amides via Bidentate-Chelation Assistance [J].

Aihara, Yoshinori ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (03) :898-901

[5] Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].

Aihara, Yoshinori ;

Chatani, Naoto .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311

[6]

[Anonymous], 2016, Angew. Chem. Int. Ed

[7]

[Anonymous], ANGEW CHEM

[8]

[Anonymous], 2011, ANGEW CH

[9]

[Anonymous], 2013, Angew. Chem, DOI DOI 10.1002/ANGE.201301451

[10] The first Suzuki cross-couplings of aryltrimethylammonium salts [J].

Blakey, SB ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6046-6047

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