Palladium-Catalyzed Regioselective Arylation of 1,1,3-Triaryl-2-azaallyl Anions with Aryl Chlorides

被引:59
作者
Li, Minyan [1 ]
Berritt, Simon [1 ]
Walsh, Patrick J. [1 ]
机构
[1] Univ Penn, Dept Chem, Roy & Diana Vagelos Labs, Penn Merck Lab High Throughput Expt, Philadelphia, PA 19104 USA
基金
美国国家科学基金会; 美国国家卫生研究院;
关键词
ALLYL DIPHENYLGLYCINATE IMINES; OXIDATIVE ADDITION; DECARBOXYLATIVE ALLYLATION; LIGAND; COMPLEX; HALIDE; MECHANISM;
D O I
10.1021/ol502043j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A regioselective arylation of 1,1,3-triaryl-2-azaallyl anions with aryl chlorides is described. The palladium-NIXANTPHOS-based catalyst affords diarylmethylamine derivatives in good yield and without product isomerization. A gram scale sequential one-pot ketimine synthesis/arylation protocol was also developed.
引用
收藏
页码:4312 / 4315
页数:4
相关论文
共 36 条
[1]   Oxidative addition of aryl chlorides to monoligated palladium(0): A DFT-SCRF study [J].
Ahlquist, Marten ;
Norrby, Per-Ola .
ORGANOMETALLICS, 2007, 26 (03) :550-553
[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]   Distinct mechanisms for the oxidative addition of chloro-, bromo-, and lodoarenes to a bisphosphine palladium(0) complex with hindered ligands [J].
Barrios-Landeros, F ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (19) :6944-6945
[4]   Effect of Ligand Steric Properties and Halide Identity on the Mechanism for Oxidative Addition of Haloarenes to Trialkylphosphine Pd(0) Complexes [J].
Barrios-Landeros, Fabiola ;
Carrow, Brad P. ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (23) :8141-8154
[5]   Bite angle effects of diphosphines in C-C and C-X bond forming cross coupling reactions [J].
Birkholz , Mandy-Nicole ;
Freixa, Zoraida ;
van Leeuwen, Piet W. N. M. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (04) :1099-1118
[6]   Synthesis and Application of Palladium Precatalysts that Accommodate Extremely Bulky Di-tert-butylphosphino Biaryl Ligands [J].
Bruno, Nicholas C. ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2013, 15 (11) :2876-2879
[7]   Design and preparation of new palladium precatalysts for C-C and C-N cross-coupling reactions [J].
Bruno, Nicholas C. ;
Tudge, Matthew T. ;
Buchwald, Stephen L. .
CHEMICAL SCIENCE, 2013, 4 (03) :916-920
[8]   Synthesis of homoallylic amines via the palladium-catalyzed decarboxylative coupling of amino acid derivatives [J].
Burger, Erin C. ;
Tunge, Jon A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (31) :10002-10003
[9]   The relaxing effect of BDF 9148 on the KCl-contracted aorta isolated from normo- and hyper-tensive rats [J].
Doggrell, SA ;
Liang, LC .
NAUNYN-SCHMIEDEBERGS ARCHIVES OF PHARMACOLOGY, 1998, 357 (02) :126-132
[10]   One-Pot Tandem Decarboxylative Allylation-Heck Cyclization of Allyl Diphenylglycinate Imines: Rapid Access to Polyfunctionalized 1-Aminoindanes [J].
Fields, Wendy H. ;
Khan, Ali K. ;
Sabat, Michal ;
Chruma, Jason J. .
ORGANIC LETTERS, 2008, 10 (22) :5131-5134