Readily available catalysts for demanding Suzuki-Miyaura couplings under mild conditions

被引:26
作者
Demchuk, Oleg M. [1 ]
Kaplon, Katarzyna [1 ]
Mazur, Liliana [1 ]
Strzelecka, Dorota [1 ]
Pietrusiewicz, K. Michal [1 ]
机构
[1] Marie Curie Sklodowska Univ, Dept Organ Chem, 33 Gliniana St, PL-20614 Lublin, Poland
关键词
Cross-coupling; C; P-complexation; Aqueous media; Suzuld-Miyaura coupling; Heck reaction; Catalyst structure; BIARYL NATURAL-PRODUCTS; RATIONAL LIGAND DESIGN; 2-AMINO-2'-DIPHENYLPHOSPHINO-1,1'-BINAPHTHYL MAP; CROSS-COUPLINGS; CHEMISTRY; GREEN; WATER; HECK; PHOSPHINES; COMPLEXES;
D O I
10.1016/j.tet.2016.08.087
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A straightforward synthesis of a sterically hindered and electron rich bidentate monophosphine biaryl ligand Sym-Phos of C,P-type of complexation was realised in a high yield starting from simple substrates in easily affordable conditions. In combination with a palladium source, the obtained ligand formed a highly active catalyst mediating sterically demanding Suzuki-Miyaura coupling reactions in aqueous media even at 60 degrees C and with no need to protect the reaction mixture by an inert gas. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6668 / 6677
页数:10
相关论文
共 54 条
[1]  
Ackermann L., 2009, MODERN ARVLATION MET
[2]  
Agilent, 2013, CRYSALIS PRO
[3]   Pd-catalyzed Suzuki-Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands [J].
Altman, Ryan A. ;
Buchwald, Stephen L. .
NATURE PROTOCOLS, 2007, 2 (12) :3115-3121
[4]   Mechanistic and kinetic studies of palladium catalytic systems [J].
Amatore, C ;
Jutand, A .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 576 (1-2) :254-278
[5]  
[Anonymous], 2012, ANGEW CHEM, V124, P5150
[6]  
[Anonymous], CCDC1448447
[7]   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
[8]   Rationale behind the resistance of dialkylbiaryl phosphines toward oxidation by molecular oxygen [J].
Barder, Timothy E. ;
Buchwald, Stephen L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (16) :5096-5101
[9]   Structural insights into active catalyst structures and oxidative addition to (biaryl)phosphine - Palladium complexes via density functional theory and experimental studies [J].
Barder, Timothy E. ;
Biscoe, Mark R. ;
Buchwald, Stephen L. .
ORGANOMETALLICS, 2007, 26 (09) :2183-2192
[10]   Modified BINAP: The how and the why [J].
Berthod, M ;
Mignani, G ;
Woodward, G ;
Lemaire, M .
CHEMICAL REVIEWS, 2005, 105 (05) :1801-1836