Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group

被引:83
作者
Chan, Li Yan [1 ]
Kim, Sunggak [1 ]
Ryu, Taekyu [2 ]
Lee, Phil Ho [2 ]
机构
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
[2] Kangwon Natl Univ, Dept Chem, Chunchon 200701, South Korea
基金
新加坡国家研究基金会;
关键词
C-H ACTIVATION; ORTHO-LITHIATION; HECK REACTION; ROOM-TEMPERATURE; ORTHO-ARYLATION; ARENES; BONDS; FUNCTIONALIZATION; OLEFINATION; PHENOLS;
D O I
10.1039/c3cc41107a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient Pd-catalyzed ortho-alkenylation is reported using a mono-phosphoric acid-directing group for the first time. This phosphoric acid-directing group is successfully utilized for the synthesis of various alkenylated products and offers a new approach to transition-metal-catalyzed C-H activation.
引用
收藏
页码:4682 / 4684
页数:3
相关论文
共 77 条
[1]   Palladium-Catalyzed Direct ortho-Alkynylation of Aromatic Carboxylic Acid Derivatives [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
ORGANIC LETTERS, 2012, 14 (01) :354-357
[2]   Palladium-Catalyzed Direct Ethynylation of C(sp3)-H Bonds in Aliphatic Carboxylic Acid Derivatives [J].
Ano, Yusuke ;
Tobisu, Mamoru ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12984-12986
[3]   The catalytic intermolecular orthoarylation of phenols [J].
Bedford, RB ;
Coles, SJ ;
Hursthouse, MB ;
Limmert, ME .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (01) :112-114
[4]   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
[5]   The heck reaction as a sharpening stone of palladium catalysis [J].
Beletskaya, IP ;
Cheprakov, AV .
CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066
[6]   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
[7]   Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].
Chen, X ;
Li, JJ ;
Hao, XS ;
Goodhue, CE ;
Yu, JQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79
[8]   PyDipSi: A General and Easily Modifiable/Traceless Si-Tethered Directing Group for C-H Acyloxylation of Arenes [J].
Chernyak, Natalia ;
Dudnik, Alexander S. ;
Huang, Chunhui ;
Gevorgyan, Vladimir .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) :8270-+
[9]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[10]   Divergent C-H Functionalizations Directed by Sulfonamide Pharmacophores: Late-Stage Diversification as a Tool for Drug Discovery [J].
Dai, Hui-Xiong ;
Stepan, Antonia F. ;
Plummer, Mark S. ;
Zhang, Yang-Hui ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) :7222-7228