Exploiting the Divergent Reactivity of Aryl-Palladium Intermediates for the Rapid Assembly of Fluorene and Phenanthrene Derivatives

被引:141
作者
Zhao, Ya-Bin [1 ]
Mariampillai, Brian [1 ]
Candito, David A. [1 ]
Laleu, Benoit [1 ]
Li, Mengzhou [1 ]
Lautens, Mark [1 ]
机构
[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada
基金
瑞士国家科学基金会; 加拿大自然科学与工程研究理事会;
关键词
annulation; C-H activation; domino reactions; homogeneous catalysis; palladium; INTRAMOLECULAR NUCLEOPHILIC-ADDITION; CATALYZED ALPHA-ARYLATION; ARYLBORONIC ACIDS; SUZUKI-MIYAURA; KETONES; ALKYNES; CYCLIZATION; SUBSTITUTION; ANNULATION; COMPLEXES;
D O I
10.1002/anie.200805780
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
They all fall down: The value of domino processes can be greatly enhanced when the possibility exists for one to selectively diverge from a common intermediate. In preliminary studies the dual reactivity of aryl-palladium intermediates is exploited. A diverse array of fluorene and phenanthrene derivatives were synthesized in a rapid and efficient manner (see scheme). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1849 / 1852
页数:4
相关论文
共 44 条
[1]  
Ackermann L., 2006, Angew. Chem, V118, P7789
[2]   A diaminochlorophosphine for palladium-catalyzed arylations of amines and ketones [J].
Ackermann, Lutz ;
Spatz, Julia H. ;
Gschrei, Christian J. ;
Born, Robert ;
Althammer, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) :7627-7630
[3]  
[Anonymous], ANGEW CHEM
[4]   Aryl transfer between Pd(II) centers or Pd(IV) intermediates in Pd-catalyzed domino reactions [J].
Cárdenas, DJ ;
Martín-Matute, B ;
Echavarren, AM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (15) :5033-5040
[5]   Recent developments in catalytic aryl coupling reactions [J].
Catellani, Marta ;
Motti, Elena ;
Della Ca, Nicola ;
Ferraccioli, Raffaella .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (25) :4153-4165
[6]   Nickel-catalyzed asymmetric α-arylation of ketone enolates [J].
Chen, GS ;
Kwong, FY ;
Chan, HO ;
Yu, WY ;
Chan, ASC .
CHEMICAL COMMUNICATIONS, 2006, (13) :1413-1415
[7]   Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].
Culkin, DA ;
Hartwig, JF .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245
[8]   Diastereoselective synthesis of arylglycine derivatives by cationic Palladium(II)-Catalyzed addition of arylboronic acids to N-tert-Butanesulfinyl imino esters [J].
Dai, Huixiong ;
Lu, Xiyan .
ORGANIC LETTERS, 2007, 9 (16) :3077-3080
[9]   Palladium-catalysed synthesis of nonsymmetrically disubstituted-1,1′-biphenyls from o-substituted aryl iodides through aryl coupling and delayed hydrogenolysis [J].
Deledda, S ;
Motti, E ;
Catellani, M .
CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (6-7) :741-747
[10]   A new reaction sequence involving palladium-catalyzed unsymmetrical aryl coupling [J].
Faccini, F ;
Motti, E ;
Catellani, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (01) :78-79