Iridium-Catalyzed ortho-C(sp2)-H Amidation of Benzaldehydes with Organic Azides

被引：53

作者：

Mu, Delong ^{[1
,2
]}

Wang, Xinmou ^{[1
,2
]}

Chen, Gong ^{[1
,2
,3
]}

He, Gang ^{[1
,2
]}

机构：

[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300071, Peoples R China

[3] Penn State Univ, Dept Chem, University Pk, PA 16802 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 82卷 / 08期

关键词：

C-H AMIDATION; N-SULFONYL; 2-AMINOBENZALDEHYDES; DIRECT ORTHO-ALKENYLATION; DIRECTING GROUP; SIMPLE OLEFINS; PRIMARY AMINES; ALDEHYDES; FUNCTIONALIZATION; ACTIVATION; AMINATION;

D O I：

10.1021/acs.joc.7b00531

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium-catalyzed ortho-C(sp(2))-H amidation reaction of benzaldehydes with organic azides has been developed. A catalytic amount of 3,5-di(trifluoromethyl)aniline was used to promote the Ir-catalyzed directed C-H amination reaction through a transient aldimine intermediate. This reaction tolerates a broad scope of benzaldehyde substrates and works well with a range of aryl- and alkylsulfonyl azides.

引用

页码：4497 / 4503

页数：7

共 52 条

[1] Acylsilanes in Iridium-Catalyzed Directed Amidation Reactions and Formation of Heterocycles via Siloxycarbenes [J].

Becker, Peter ;

Pirwerdjan, Ramona ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (51) :15493-15496

[2] Ru(II)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides [J].

Bhanuchandra, M. ;

Yadav, M. Ramu ;

Rit, Raja K. ;

Kuram, Malleswara Rao ;

Sahoo, Akhila K. .

CHEMICAL COMMUNICATIONS, 2013, 49 (45) :5225-5227

[3] Formal Ir-Catalyzed Ligand-Enabled Ortho and Meta Borylation of Aromatic Aldehydes via in Situ-Generated Imines [J].

Bisht, Ranjana ;

Chattopadhyay, Buddhadeb .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (01) :84-87

[4] Rhodium-Catalyzed Direct Annulation of Aldehydes with Alkynes Leading to Indenones: Proceeding through in Situ Directing Group Formation and Removal [J].

Chen, Shuyou ;

Yu, Jintao ;

Jiang, Yan ;

Chen, Fan ;

Cheng, Jiang .

ORGANIC LETTERS, 2013, 15 (18) :4754-4757

[5] Efficient and General Synthesis of 3-Aminoindolines and 3-Aminoindoles via Copper-Catalyzed Three-Component Coupling Reaction [J].

Chernyak, Dmitri ;

Chernyak, Natalia ;

Gevorgyan, Vladimir .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (06) :961-966

[6] Selective palladium-catalyzed arylation(s) of benzaldehyde derivatives by N-heterocarbene ligands [J].

Gürbüz, N ;

Özdemir, I ;

Çetinkaya, B .

TETRAHEDRON LETTERS, 2005, 46 (13) :2273-2277

[7] Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides [J].

Hartwig, John F. .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1534-1544

[8] Regioselective Introduction of Heteroatoms at the C-8 Position of Quinoline N-Oxides: Remote C-H Activation Using N-Oxide as a Stepping Stone [J].

Hwang, Heejun ;

Kim, Jinwoo ;

Jeong, Jisu ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (30) :10770-10776

[9] Organic azides: "energetic reagents'' for the intermolecular amination of C-H bonds [J].

Intrieri, Daniela ;

Zardi, Paolo ;

Caselli, Alessandro ;

Gallo, Emma .

CHEMICAL COMMUNICATIONS, 2014, 50 (78) :11440-11453

[10] C-H and C-C bond activation of primary amines through dehydrogenation and transimination [J].

Jun, CH ;

Chung, KY ;

Hong, JB .

ORGANIC LETTERS, 2001, 3 (05) :785-787

← 1 2 3 4 5 6 →