Rhodium-Catalyzed Selective C-H Activation/Olefination of Phenol Carbamates

被引：174

作者：

Gong, Tian-Jun ^{[1
]}

Xiao, Bin ^{[1
,2
]}

Liu, Zhao-Jing ^{[1
]}

Wan, Jian ^{[1
]}

Xu, Jun ^{[1
]}

Luo, Dong-Fen ^{[1
]}

Fu, Yao ^{[1
]}

Liu, Lei ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Joint Lab Green Synthet Chem, Hefei 230026, Peoples R China

[2] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 12期

关键词：

INTERNAL ALKYNES; BOND ACTIVATION; OLEFINATION; FUNCTIONALIZATION; ARENES; ACIDS; COUPLING/CYCLIZATION; ALKENYLATION; TEMPERATURE; DERIVATIVES;

D O I：

10.1021/ol201140q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rh(III)-catalyzed ortho C-H activation/olefination of phenol carbamates has been developed. High regioselectivity is observed with a range of phenol carbamates enabling efficient coupling with acrylates and styrenes. This reaction exhibits different reactivity as compared to the Pd-catalyzed ortho-arylation reaction of phenol esters and provides a new approach for the synthesis of ortho-substituted phenols.

引用

页码：3235 / 3237

页数：3

共 36 条

[1]

[Anonymous], ANGEW CHEM INT ED

[2] Palladium-catalysed ortho-arylation of carbamate-protected phenols [J].

Bedford, Robin B. ;

Webster, Ruth L. ;

Mitchell, Charlotte J. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (23) :4853-4857

[3] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].

Boele, MDK ;

van Strijdonck, GPF ;

de Vries, AHM ;

Kamer, PCJ ;

de Vries, JG ;

van Leeuwen, PWNM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587

[4] Palladium-catalyzed C-H functionalization of pyridine N-oxides:: Highly selective alkenylation and direct arylation with unactivated arenes [J].

Cho, Seung Hwan ;

Hwang, Seung Jun ;

Chang, Sukbok .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9254-+

[5] AROMATIC SUBSTITUTION OF OLEFIN .3. REACTION OF STYRENE-PALLADIUM(2) CHLORIDE COMPLEX [J].

FUJIWARA, Y ;

MORITANI, I ;

MATSUDA, M .

TETRAHEDRON, 1968, 24 (13) :4819-&

[6] Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C-H bond cleavage [J].

Fukutani, Tatsuya ;

Umeda, Nobuyoshi ;

Hirano, Koji ;

Satoh, Tetsuya ;

Miura, Masahiro .

CHEMICAL COMMUNICATIONS, 2009, (34) :5141-5143

[7] Palladium-catalyzed intermolecular alkenylation of indoles by solvent-controlled regioselective C-H functionalization [J].

Grimster, NP ;

Gauntlett, C ;

Godfrey, CRA ;

Gaunt, MJ .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3125-3129

[8] Rhodium-Catalyzed Direct Oxidative Carbonylation of Aromatic C-H Bond with CO and Alcohols [J].

Guan, Zheng-Hui ;

Ren, Zhi-Hui ;

Spinella, Stephen M. ;

Yu, Shichao ;

Liang, Yong-Min ;

Zhang, Xumu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (02) :729-733

[9] Rhodium(III)-Catalyzed Isoquinolone Synthesis: The N-O Bond as a Handle for C-N Bond Formation and Catalyst Turnover [J].

Guimond, Nicolas ;

Gouliaras, Christina ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (20) :6908-+

[10] Isoquinoline Synthesis via Rhodium-Catalyzed Oxidative Cross-Coupling/Cyclization of Aryl Aldimines and Alkynes [J].

Guimond, Nicolas ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (34) :12050-+

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