Copper-Catalyzed Oxidative -Ketoacylations of Sulfoximines with Aryl Methyl Ketones and Dioxygen as Terminal Oxidant

被引：19

作者：

Cheng, Hanchao ^{[1
]}

Bolm, Carsten ^{[1
]}

机构：

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

来源：

SYNLETT | 2016年 / 27卷 / 05期

关键词：

sulfoximine; ketone; dioxygen; oxidative coupling; -ketoacylation; ALPHA-OXOCARBOXYLIC ACIDS; SOLVENT-FREE CONDITIONS; C BOND-CLEAVAGE; EFFICIENT SYNTHESIS; PROTEASE INHIBITOR; MOLECULAR-OXYGEN; ROOM-TEMPERATURE; METAL-FREE; KETOAMIDES; AMINES;

D O I：

10.1055/s-0035-1560989

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient copper-catalyzed C-H/N-H bond functionalization for the synthesis of -keto-N-acyl sulfoximines from aryl methyl ketones and NH-sulfoximines with molecular oxygen as terminal oxidant has been developed.

引用

页码：769 / 772

页数：4

共 49 条

[11] A Palladium(II)-Catalyzed Synthesis of α-Ketoamides via Chemoselective Aroyl Addition to Cyanamides [J].

Guin, Srimanta ;

Rout, Saroj Kumar ;

Gogoi, Anupal ;

Ali, Wajid ;

Patel, Bhisma K. .

ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (11-12) :2559-2565

[12] Reactions of a carbamoylstannane with acid chlorides:: Highly efficient synthesis of α-oxo amides [J].

Hua, RM ;

Takeda, H ;

Abe, Y ;

Tanaka, M .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (03) :974-976

[13] From Ketones to Esters by a Cu-Catalyzed Highly Selective C(CO)-C(alkyl) Bond Cleavage: Aerobic Oxidation and Oxygenation with Air [J].

Huang, Xiaoqiang ;

Li, Xinyao ;

Zou, Miancheng ;

Song, Song ;

Tang, Conghui ;

Yuan, Yizhi ;

Jiao, Ning .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (42) :14858-14865

[14] Clinical Pharmacology Profile of Boceprevir, a Hepatitis C Virus NS3 Protease Inhibitor: Focus on Drug-Drug Interactions [J].

Khalilieh, Sauzanne ;

Feng, Hwa-Ping ;

Hulskotte, Ellen G. J. ;

Wenning, Larissa A. ;

Butterton, Joan R. .

CLINICAL PHARMACOKINETICS, 2015, 54 (06) :599-614

[15] Substrate derived peptidic α-ketoamides as inhibitors of the malarial protease PfSUB1 [J].

Kher, Samir S. ;

Penzo, Maria ;

Fulle, Simone ;

Finn, Paul W. ;

Blackman, Michael J. ;

Jirgensons, Aigars .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (18) :4486-4489

[16] Copper(II)-Triflate-Catalyzed Oxidative Amidation of Terminal Alkynes: A General Approach to α-Ketoamides [J].

Kumar, Manjeet ;

Devari, Shekaraiah ;

Kumar, Arvind ;

Sultan, Shaista ;

Ahmed, Qazi Naveed ;

Rizvi, Masood ;

Shah, Bhahwal Ali .

ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 4 (05) :438-441

[17] Hydroxyl Radical-Mediated Novel Modification of Peptides: N-Terminal Cyclization through the Formation of α-Ketoamide [J].

Lee, Seon Hwa ;

Kyung, Hyunsook ;

Yokota, Ryo ;

Goto, Takaaki ;

Oe, Tomoyuki .

CHEMICAL RESEARCH IN TOXICOLOGY, 2015, 28 (01) :59-70

[18] Cu(II)-catalyzed decarboxylative acylation of acyl C-H of formamides with α-oxocarboxylic acids leading to α-ketoamides [J].

Li, Dengke ;

Wang, Min ;

Liu, Jie ;

Zhao, Qiong ;

Wang, Lei .

CHEMICAL COMMUNICATIONS, 2013, 49 (35) :3640-3642

[19] Formamidine hydrochloride as an amino surrogate: I2-catalyzed oxidative amidation of aryl methyl ketones leading to free (N-H) α-ketoamides [J].

Liu, Shan ;

Gao, Qinghe ;

Wu, Xia ;

Zhang, Jingjing ;

Ding, Kerong ;

Wu, Anxin .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (08) :2239-2242

[20] nBu4NI-catalyzed direct synthesis of α-ketoamides from aryl methyl ketones with dialkylformamides in water using TBHP as oxidant [J].

Mai, Wen-Peng ;

Wang, Hui-Hui ;

Li, Zhi-Cheng ;

Yuan, Jin-Wei ;

Xiao, Yong-Mei ;

Yang, Liang-Ru ;

Mao, Pu ;

Qu, Ling-Bo .

CHEMICAL COMMUNICATIONS, 2012, 48 (81) :10117-10119

← 1 2 3 4 5 →