Rhodium(III)-catalyzed C-H alkynylation of azomethine ylides under mild conditions

被引：40

作者：

Zhang, Xueyun ^{[1
,2
]}

Qi, Zisong ^{[2
]}

Gao, Jian ^{[1
]}

Li, Xingwei ^{[2
]}

机构：

[1] Qilu Univ Technol, Sch Chem & Pharmaceut Engn, Jinan 250353, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 46期

关键词：

CATALYZED DIRECT ALKYNYLATION; TERMINAL ALKYNES; BOND FORMATION; GOLD; ACTIVATION; CASCADE; 2-ALKYNYLBENZALDEHYDE; FUNCTIONALIZATION; ISOQUINOLINES; ALKENES;

D O I：

10.1039/c4ob01596g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh(III)-catalyzed efficient C-H alkynylation of azomethine imines with alkynylated hypervalent iodine is developed under mild conditions. A broad scope of azomethine imines and alkyne substrates is established. The azomethine acts as a masked aldehyde and circumvents its poor directing effect.

引用

页码：9329 / 9332

页数：4

共 51 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] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[3] "Two Functional Groups in One Package": Using Both Alkyne π-Bonds in Cascade Transformations [J].

Alabugin, Igor V. ;

Gold, Brian .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (16) :7777-7784

[4] Ruthenium-Catalyzed Direct ortho-Alkynylation of Arenes with Chelation Assistance [J].

Ano, Yusuke ;

Tobisu, Mamoru ;

Chatani, Naoto .

SYNLETT, 2012, (19) :2763-2767

[5] Synthesis of Triazolo Isoquinolines and Isochromenes from 2-Alkynylbenzaldehyde via Domino Reactions under Transition-Metal-Free Conditions [J].

Arigela, Rajesh K. ;

Sarnala, Srinivas ;

Mahar, Rohit ;

Shukla, Sanjeev K. ;

Kundu, Bijoy .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (20) :10476-10484

[6]

Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153j, 10.1021/cr300153J]

[7] Para-Selective Gold-Catalyzed Direct Alkynylation of Anilines [J].

Brand, Jonathan P. ;

Waser, Jerome .

ORGANIC LETTERS, 2012, 14 (03) :744-747

[8] Direct Alkynylation of Thiophenes: Cooperative Activation of TIPS-EBX with Gold and Bronsted Acids [J].

Brand, Jonathan P. ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7304-7307

[9] Direct Alkynylation of Indole and Pyrrole Heterocycles [J].

Brand, Jonathan P. ;

Charpentier, Julie ;

Waser, Jerome .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (49) :9346-9349

[10] Rhodium(III)-Catalyzed Annulation of Azomethine Ylides with Alkynes via CH Activation [J].

Chen, Yuye ;

Wang, Fen ;

Zhen, Wencui ;

Li, Xingwei .

ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) :353-359

← 1 2 3 4 5 6 →