Acylsilanes in Iridium-Catalyzed Directed Amidation Reactions and Formation of Heterocycles via Siloxycarbenes

被引：81

作者：

Becker, Peter ^{[1
]}

Pirwerdjan, Ramona ^{[1
]}

Bolm, Carsten ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 51期

关键词：

acylsilanes; carbenes; C-H functionalization; heterocyclic chemistry; iridium catalysis; C-H AMIDATION; SULFONAMIDE-AMINOSULFONE REARRANGEMENT; PHOTO-FRIES REARRANGEMENT; AROMATIC AZO-COMPOUNDS; SULFONYL AZIDES; MOLECULAR-REARRANGEMENTS; SYNTHETIC ROUTE; NITROGEN-SOURCE; ARYL AZIDES; KETONES;

D O I：

10.1002/anie.201508501

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Exposing ortho-amido aroylsilanes to visible light or heat leads to cyclization reactions that provide N-heterocyclic compounds via siloxycarbenes as key intermediates. The previously unreported starting materials have been prepared by directed amidations of aromatic acylsilanes in the presence of an iridium catalyst followed by N-alkylation.

引用

页码：15493 / 15496

页数：4

共 50 条

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

Ackermann, Lutz .

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

[2]

[Anonymous], ANGEW CHEM

[3]

[Anonymous], 2014, ANGEW CHEM, V126, P2235

[4] MOLECULAR-REARRANGEMENTS .19. THERMOLYSIS AND PHOTOLYSIS OF N-ARYLBENZENESULFONAMIDES [J].

BADR, MZA ;

ALY, MM ;

FAHMY, AM .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4784-4787

[5] SILOXYCARBENES FROM THERMOLYSIS OF ACYLSILANES [J].

BASSINDALE, AR ;

BROOK, AG ;

HARRIS, J .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 90 (01) :C6-C7

[6]

Becker P., 2014, ANGEW CHEM, V126, P273

[7] Photochemical Intermolecular Silylacylations of Electron-Deficient Internal Alkynes [J].

Becker, Peter ;

Priebbenow, Daniel L. ;

Zhang, Hui-Jun ;

Pirwerdjan, Ramona ;

Bolm, Carsten .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (02) :814-817

[8] Acylsilanes in Rhodium(III)-Catalyzed Directed Aromatic C-H Alkenylations and Siloxycarbene Reactions with C-C Double Bonds [J].

Becker, Peter ;

Priebbenow, Daniel L. ;

Pirwerdjan, Ramona ;

Bolm, Carsten .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (01) :269-271

[9] 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

[10] SOME MOLECULAR-REARRANGEMENTS OF ORGANOSILICON COMPOUNDS [J].

BROOK, AG .

ACCOUNTS OF CHEMICAL RESEARCH, 1974, 7 (03) :77-84

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