Chemoselective and Regiospecific Suzuki Coupling on a Multisubstituted sp3-Carbon in 1,1-Diborylalkanes at Room Temperature

被引:180
作者
Endo, Kohei [1 ]
Ohkubo, Takahiro [2 ]
Hirokami, Munenao [2 ]
Shibata, Takanori [2 ]
机构
[1] Waseda Inst Adv Study, Shinjuku Ku, Tokyo 1698050, Japan
[2] Waseda Univ, Dept Chem & Biochem, Sch Adv Sci & Engn, Shinjuku Ku, Tokyo 1698555, Japan
基金
日本学术振兴会;
关键词
CROSS-COUPLINGS; ACID-DERIVATIVES; MILD CONDITIONS; BORONIC ACIDS; ALKYL-HALIDES; PALLADIUM; ARYL; ESTERS; HYDROBORATION; ALKENYLBORONATE;
D O I
10.1021/ja105176v
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The palladium-catalyzed Suzuki-Miyaura cross-coupling on a multisubstituted sp(3)-carbon in 1,1-diborylalkanes was achieved at room temperature. The generation of a monoborate intermediate by virtue of the adjacent B atom could result in the chemoselective coupling reaction under ambient conditions.
引用
收藏
页码:11033 / 11035
页数:3
相关论文
共 39 条
[1]   Palladium catalysts for the Suzuki cross-coupling reaction: An overview of recent advances [J].
Bellina, F ;
Carpita, A ;
Rossi, R .
SYNTHESIS-STUTTGART, 2004, (15) :2419-2440
[2]  
Chemler SR, 2001, ANGEW CHEM INT EDIT, V40, P4544, DOI 10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO
[3]  
2-N
[4]   General Method for Synthesis of 2-Heterocyclic N-Methyliminodiacetic Acid Boronates [J].
Dick, Graham R. ;
Knapp, David M. ;
Gillis, Eric P. ;
Burke, Martin D. .
ORGANIC LETTERS, 2010, 12 (10) :2314-2317
[5]   Suzuki-Miyaura cross-coupling reactions of alkylboronic acid derivatives or alkyltrifluoroborates with aryl, alkenyl or alkyl halides and triflates [J].
Doucet, Henri .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (12) :2013-2030
[6]   Efficient cross-coupling of secondary alkyltrifluoroborates with aryl chlorides-reaction discovery using parallel microscale experimentation [J].
Dreher, Spencer D. ;
Dormer, Peter G. ;
Sandrock, Deidre L. ;
Molander, Gary A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9257-+
[7]   Stereoselective Synthesis of Tetrasubstituted Alkenylboronates via 1,1-Organodiboronates [J].
Endo, Kohei ;
Hirokami, Munenao ;
Shibata, Takanori .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (10) :3469-3472
[8]   Synthesis of 1,1-Organodiboronates via Rh(I)Cl-Catalyzed Sequential Regioselective Hydroboration of 1-Alkynes [J].
Endo, Kohei ;
Hirokami, Munenao ;
Shibata, Takanori .
SYNLETT, 2009, (08) :1331-1335
[9]   A simple and modular strategy for small molecule synthesis: Iterative Suzuki-Miyaura coupling of B-protected haloboronic acid building blocks [J].
Gillis, Eric P. ;
Burke, Martin D. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (21) :6716-+
[10]   Diastereoselective Addition of Zincated Hydrazones to Alkenylboronates and Stereospecific Trapping of Boron/Zinc Bimetallic Intermediates by Carbon Electrophiles [J].
Hatakeyama, Takuji ;
Nakamura, Masaharu ;
Nakamura, Eichi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (46) :15688-15701