Recent advances in direct arylation via palladium-catalyzed aromatic C-H activation

被引:656
作者
Li, Bi-Jie
Yang, Shang-Dong
Shi, Zhang-Jie [1 ]
机构
[1] Peking Univ, Beijing Natl Lab Mol Sci, Minist Educ, Coll Chem, Beijing 100871, Peoples R China
关键词
C-H activation; arylation; palladium; catalysis; acetanilide;
D O I
10.1055/s-2008-1042907
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly selective arylation catalyzed by palladium and directed by the acetamino group provides an efficient and practical protocol for constructing unique biaryl scaffolds, which could be further transformed into different structural units found in a range of natural products. 1 Introduction 2 Highly Regioselective Halogenation 3 Highly Regioselective Arylation 3.1 With Arylboronic Acids 3.2 With Trialkoxyarylsilanes 3.3 With Simple Arenes 3.4 Further Transformations 4 Conclusion.
引用
收藏
页码:949 / 957
页数:9
相关论文
共 103 条
[1]   Solvent-less and fluoride-free hiyama reaction of arylsiloxanes with aryl bromides and chlorides promoted by sodium hydroxide:: A useful protocol for palladium recycling and product isolation [J].
Alacid, Emilio ;
Najera, Carmen .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (7-8) :945-952
[2]   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
[3]   Diastereoselective alkylation of (arene)tricarbonylchromium and ferrocene complexes using a chiral, C2-symmetrical 1,2-diamine as auxiliary [J].
Alexakis, A ;
Tomassini, A ;
Andrey, O ;
Bernardinelli, G .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (07) :1332-1339
[4]  
[Anonymous], 1898, BER DTSCH CHEM GES
[5]   ACTIVATION OF ARENE CARBON HYDROGEN-BONDS - HIGHLY REGIOSELECTIVE, ELECTROPHILIC AROMATIC METALATION WITH RHODIUM(III) PORPHYRIN AND SUBSEQUENT CLEAVAGE OF CARBON RHODIUM BOND [J].
AOYAMA, Y ;
YOSHIDA, T ;
SAKURAI, K ;
OGOSHI, H .
ORGANOMETALLICS, 1986, 5 (01) :168-173
[6]   Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature [J].
Boele, MDK ;
van Strijdonck, GPF ;
de Vries, AHM ;
Kamer, PCJ ;
de Vries, JG ;
van Leeuwen, PWNM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) :1586-1587
[7]   MARINE HALOPEROXIDASES [J].
BUTLER, A ;
WALKER, JV .
CHEMICAL REVIEWS, 1993, 93 (05) :1937-1944
[8]   Ru3(CO)12-catalyzed coupling reaction of sp3 C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes [J].
Chatani, N ;
Asaumi, T ;
Yorimitsu, S ;
Ikeda, T ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (44) :10935-10941
[9]   Carbonylation at sp3 C-H bonds adjacent to a nitrogen atom in alkylamines catalyzed by rhodium complexes [J].
Chatani, N ;
Asaumi, T ;
Ikeda, T ;
Yorimitsu, S ;
Ishii, Y ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (51) :12882-12883
[10]   Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter [J].
Chen, X ;
Li, JJ ;
Hao, XS ;
Goodhue, CE ;
Yu, JQ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (01) :78-79