Copper-Catalyzed C-C Bond Formation through C-H Functionalization: Synthesis of Multisubstituted Indoles from N-Aryl Enaminones

被引:315
作者
Bernini, Roberta [2 ,3 ]
Fabrizi, Giancarlo [1 ]
Sferrazza, Alessio [1 ]
Cacchi, Sandro [1 ]
机构
[1] Univ Rome, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy
[2] Univ Tuscia, Dipartimento ABAC, Viterbo, Italy
[3] Consorzio Univ La Chim Ambiente, Viterbo, Italy
关键词
C-C coupling; copper; heterogeneous catalysis; indoles; synthesis design; CONJUGATE REDUCTION; DIRECT ARYLATIONS; ACTIVATION; AMINATION; CYCLIZATION; ANALOGS; ESTERS;
D O I
10.1002/anie.200902440
中图分类号
O6 [化学];
学科分类号
070301 [无机化学];
摘要
A variety of functionalities, including the whole range of halogen substituents, are tolerated in the title reaction, an intramolecular approach for the construction of a multisubstituted indole skeleton from readily available enaminones (see scheme; phen=1,10-phenanthroline). The indole products are also prepared directly in high yield from α, β-ynones and primary amines. © 2009 Wiley-VCH Verlag.
引用
收藏
页码:8078 / 8081
页数:4
相关论文
共 53 条
[1]
Catalytic arylation reactions by C-H bond activation with aryl tosylates [J].
Ackermann, L ;
Althammer, A ;
Born, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (16) :2619-2622
[2]
Dehydrative Direct Arylations of Arenes with Phenols via Ruthenium-Catalyzed C-H and C-OH Bond Functionalizations [J].
Ackermann, Lutz ;
Mulzer, Michael .
ORGANIC LETTERS, 2008, 10 (21) :5043-5045
[3]
Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles [J].
Ackermann, Lutz ;
Potukuchi, Harish K. ;
Landsberg, Dirk ;
Vicente, Ruben .
ORGANIC LETTERS, 2008, 10 (14) :3081-3084
[4]
Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Althammer, Andreas .
ORGANIC LETTERS, 2008, 10 (11) :2299-2302
[5]
Catalytic arylations with challenging substrates: From air-stable HASPO preligands to indole syntheses and C-H-bond functionalizations [J].
Ackermann, Lutz .
SYNLETT, 2007, (04) :507-526
[6]
Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].
Alberico, Dino ;
Scott, Mark E. ;
Lautens, Mark .
CHEMICAL REVIEWS, 2007, 107 (01) :174-238
[7]
Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes [J].
Alonso, F ;
Beletskaya, IP ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (06) :3079-3159
[8]
[Anonymous], 2006, ANGEW CHEM
[9]
[Anonymous], 2008, ANGEW CHEM
[10]
Asymmetric conjugate reduction of α,β-unsaturated esters using a chiral phosphine-copper catalyst [J].
Appella, DH ;
Moritani, Y ;
Shintani, R ;
Ferreira, EM ;
Buchwald, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (40) :9473-9474