Nickel-Catalyzed C-O Activation of Phenol Derivatives with Potassium Heteroaryltrifluoroborates

被引:101
作者
Molander, Gary A. [1 ]
Beaumard, Floriane [1 ]
机构
[1] Univ Penn, Dept Chem, Roy & Diana A Vagelos Labs, Philadelphia, PA 19104 USA
关键词
CROSS-COUPLING REACTIONS; GENERAL PALLADIUM CATALYST; SUZUKI-MIYAURA; ARYL MESYLATES; ARYLBORONIC ACIDS; BORONIC ACIDS; ARENESULFONATES; TOSYLATES; SCOPE; COMPLEXES;
D O I
10.1021/ol101592r
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A general method based on nickel-catalyzed C-O activation of various phenol derivatives with potassium (hetero)aryltrifluoroborates has been developed. A large number of heterobiaryls can be easily obtained with yields up to 99% using methanesulfonate cross-coupling partners.
引用
收藏
页码:4022 / 4025
页数:4
相关论文
共 31 条
[1]   N,N-Diethyl O-Carbamate: Directed Metalation Group and Orthogonal Suzuki-Miyaura Cross-Coupling Partner [J].
Antoft-Finch, Aurora ;
Blackburn, Tom ;
Snieckus, Victor .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (49) :17750-17752
[2]   Catalysts for Suzuki-Miyaura coupling processes: Scope and studies of the effect of ligand structure [J].
Barder, TE ;
Walker, SD ;
Martinelli, JR ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (13) :4685-4696
[3]   A Versatile Catalyst System for Suzuki-Miyaura Cross-Coupling Reactions of C(sp2)-Tosylates and Mesylates [J].
Bhayana, Brijesh ;
Fors, Brett P. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2009, 11 (17) :3954-3957
[4]   A General Palladium Catalyst System for Suzuki-Miyaura Coupling of Potassium Aryltrifluoroborates and Aryl Mesylates [J].
Chow, Wing Kin ;
So, Chau Ming ;
Lau, Chak Po ;
Kwong, Fuk Yee .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (15) :5109-5112
[5]   Biaryl Construction via Ni-Catalyzed C-O Activation of Phenolic Carboxylates [J].
Guan, Bing-Tao ;
Wang, Yang ;
Li, Bi-Jie ;
Yu, Da-Gang ;
Shi, Zhang-Jie .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) :14468-+
[6]   A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates [J].
Knapp, David M. ;
Gillis, Eric P. ;
Burke, Martin D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (20) :6961-+
[7]   Scope and limitation of the nickel-catalyzed coupling reaction between lithium borates and mesylates [J].
Kobayashi, Y ;
William, AD ;
Mizojiri, R .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) :91-97
[8]   N-Heterocyclic Carbene Derived Nickel-Pincer Complexes: Efficient and Applicable Catalysts for Suzuki-Miyaura Coupling Reactions of Aryl/Alkenyl Tosylates and Mesylates [J].
Kuroda, Jun-ichi ;
Inamoto, Kiyofumi ;
Hiroya, Kou ;
Doi, Takayuki .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (14) :2251-2261
[9]   Mechanism of Ni-Catalyzed Selective C-O Bond Activation in Cross-Coupling of Aryl Esters [J].
Li, Zhe ;
Zhang, Song-Lin ;
Fu, Yao ;
Guo, Qing-Xiang ;
Liu, Lei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8815-8823
[10]   C-C bond formation catalyzed heterogeneously by nickel-on-graphite (Ni/Cg) [J].
Lipshutz, Bruce H. ;
Butler, Tom ;
Swift, Elizabeth .
ORGANIC LETTERS, 2008, 10 (05) :697-700