An efficient catalyst system for palladium-catalyzed borylation of aryl halides with pinacolborane

被引:80
作者
Murata, Miki [1 ]
Sambommatsu, Tomoko [1 ]
Watanabe, Shinji [1 ]
Masuda, Yuzuru [1 ]
机构
[1] Kitami Inst Technol, Dept Mat Sci, Kitami, Hokkaido 0908507, Japan
关键词
boron; palladium; catalysis; cross-coupling; ligands;
D O I
10.1055/s-2006-947365
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The combination of Pd(dba)(2) and bis(2-di-tert-butylphospbinophenyl)ether has proven to be efficient for the crosscoupling of pinacolborane with aryl bromides and chlorides. The substrate scope is broad and the present system enables the synthesis of ortho-, meta-, and para-substituted electron-rich and -deficient arylboronates.
引用
收藏
页码:1867 / 1870
页数:4
相关论文
共 19 条
[1]   Palladium-catalyzed borylation of ortho-substituted phenyl halides and application to the one-pot synthesis of 2,2′-disubstituted biphenyls [J].
Baudoin, O ;
Guénard, D ;
Guéritte, F .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (26) :9268-9271
[2]   Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis [J].
Broutin, PE ;
Cerna, I ;
Campaniello, M ;
Leroux, F ;
Colobert, F .
ORGANIC LETTERS, 2004, 6 (24) :4419-4422
[3]   A σ4, λ5-phosphinine palladium complex:: a new type of phosphorus ligand and catalyst.: Application to the Pd-catalyzed formation of arylboronic esters [J].
Doux, M ;
Mézailles, N ;
Melaimi, M ;
Ricard, L ;
Le Floch, P .
CHEMICAL COMMUNICATIONS, 2002, (15) :1566-1567
[4]   Sterically hindered chelating alkyl phosphines provide large rate accelerations in palladium-catalyzed amination of aryl iodides, bromides, and chlorides, and the first amination of aryl tosylates [J].
Hamann, BC ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (29) :7369-7370
[5]   Metal-catalyzed reactions of diborons for synthesis of organoboron compounds [J].
Ishiyama, T ;
Miyaura, N .
CHEMICAL RECORD, 2004, 3 (05) :271-280
[6]   Chemistry of Group 13 element-transition metal linkage - the platinum- and palladium-catalyzed reactions of (alkoxo)diborons [J].
Ishiyama, T ;
Miyaura, N .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 611 (1-2) :392-402
[7]   NEW DIPHOSPHINE LIGANDS BASED ON HETEROCYCLIC AROMATICS INDUCING VERY HIGH REGIOSELECTIVITY IN RHODIUM-CATALYZED HYDROFORMYLATION - EFFECT OF THE BITE ANGLE [J].
KRANENBURG, M ;
VANDERBURGT, YEM ;
KAMER, PCJ ;
VANLEEUWEN, PWNM ;
GOUBITZ, K ;
FRAANJE, J .
ORGANOMETALLICS, 1995, 14 (06) :3081-3089
[8]  
Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
[9]  
2-U
[10]   PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS [J].
MIYAURA, N ;
SUZUKI, A .
CHEMICAL REVIEWS, 1995, 95 (07) :2457-2483