Palladium-Catalyzed Carbonylation of Amines: Switchable Approaches to Carbamates and N,N'-Disubstituted Ureas

被引：77

作者：

Guan, Zheng-Hui ^{[1
]}

Lei, Hao ^{[1
]}

Chen, Ming ^{[1
]}

Ren, Zhi-Hui ^{[1
]}

Bai, Yinjuan ^{[1
]}

Wang, Yao-Yu ^{[1
]}

机构：

[1] NW Univ Xian, Key Lab Synthet & Nat Funct Mol Chem, Minist Educ, Dept Chem & Mat Sci, Xian 710069, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2012年 / 354卷 / 2-3期

基金：

中国国家自然科学基金;

关键词：

amines; carbamates; carbonylation reactions; palladium-catalyzed reactions; ureas; MASKED ISOCYANATES FACILE; OXIDATIVE CARBONYLATION; EFFICIENT SYNTHESIS; CARBON-MONOXIDE; INHIBITORS; METAL; CO;

D O I：

10.1002/adsc.201100545

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Switchable access to carbamates and ureas has been developed by solvent control palladium-catalyzed carbonylation of aromatic amines under an atmosphere of carbon monoxide. A variety of N-phenylcarbamates and N,N'-diphenylureas was easily synthesized in good to excellent yields from readily available aromatic amines under mild conditions.

引用

页码：489 / 496

页数：8

共 53 条

[1] Structure-Based Design, Synthesis, and Structure-Activity Relationship Studies of HIV-1 Protease Inhibitors Incorporating Phenyloxazolidinones [J].

Ali, Akbar ;

Reddy, G. S. Kiran Kumar ;

Nalam, Madhavi N. L. ;

Anjum, Saima Ghafoor ;

Cao, Hong ;

Schiffer, Celia A. ;

Rana, Tariq M. .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (21) :7699-7708

[2] AN EXCEPTIONALLY MILD, CATALYTIC HOMOGENEOUS METHOD FOR THE CONVERSION OF AMINES INTO CARBAMATE ESTERS [J].

ALPER, H ;

HARTSTOCK, FW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (16) :1141-1142

[3] Unsymmetrical non-adamantyl N,N-diaryl urea and amide inhibitors of soluble expoxide hydrolase [J].

Anandan, Sampath-Kumar ;

Webb, Heather K. ;

Do, Zung N. ;

Gless, Richard D. .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (15) :4259-4263

[4]

[Anonymous], 1987, J AGR FOOD CHEM

[5] CHEMISTRY OF PHOSGENE [J].

BABAD, H ;

ZEILER, AG .

CHEMICAL REVIEWS, 1973, 73 (01) :75-91

[6] Synthesis of Unsymmetrical Diarylureas via Pd-Catalyzed C-N Cross-Coupling Reactions [J].

Breitler, Simon ;

Oldenhuis, Nathan J. ;

Fors, Brett P. ;

Buchwald, Stephen L. .

ORGANIC LETTERS, 2011, 13 (12) :3262-3265

[7]

Ca N.D., 2011, J. Catal, V282, P120

[8]

Chaturvedi D, 2007, CURR ORG SYNTH, V4, P310

[9] α-pyridylation of chiral amines via urea coupling, lithiation and rearrangement [J].

Clayden, Jonathan ;

Hennecke, Ulrich .

ORGANIC LETTERS, 2008, 10 (16) :3567-3570

[10] Transition metal-catalyzed oxidative carbonylation of amines to ureas [J].

Diaz, Delmy J. ;

Darko, Ampofo K. ;

McElwee-White, Lisa .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (27) :4453-4465

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