Intramolecular direct arylation in the synthesis of fluorinated carbazoles

被引:60
作者
Bedford, Robin B. [1 ]
Betham, Michael [1 ]
Charmant, Jonathan P. H. [1 ]
Weeks, Amanda L. [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/j.tet.2008.01.143
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The amination of 2-chloroanilines with aryl bromides and subsequent intramolecular direct arylation can be exploited in the synthesis of a range of fluorinated carbazoles, where the fluorine substituent can be introduced via the aniline, the aryl bromide or both substrates. Depending on substitution patterns, the two steps can either be per-formed in tandem in one-pot under microwave heating conditions or else require a two pot approach. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6038 / 6050
页数:13
相关论文
共 34 条
[11]   Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B [J].
Bringmann, G ;
Pabst, T ;
Henschel, P ;
Kraus, J ;
Peters, K ;
Peters, EM ;
Rycroft, DS ;
Connolly, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (38) :9127-9133
[12]   THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].
BRINGMANN, G ;
WALTER, R ;
WEIRICH, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991
[13]  
*BRUK AXS, 2000, SHELXTL PROGR SYST V
[14]   Catalytic direct arylation with aryl chlorides, bromides, and iodides: Intramolecular studies leading to new intermolecular reactions [J].
Campeau, LC ;
Parisien, M ;
Jean, A ;
Fagnou, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (02) :581-590
[15]   High-yielding intramolecular direct arylation reactions with aryl chlorides [J].
Campeau, LC ;
Thansandote, P ;
Fagnou, K .
ORGANIC LETTERS, 2005, 7 (09) :1857-1860
[16]   Palladium-catalyzed intramolecular arylation of N-benzyl-2-iodoimidazoles:: A facile and rapid access to 5H-imidazo[2,1-a]isoindoles [J].
de Figueiredo, Renata Marcia ;
Thoret, Sylviane ;
Huet, Caroline ;
Dubois, Joelle .
SYNTHESIS-STUTTGART, 2007, Georg Thieme Verlag, Rudigerstrasse 14, Stuttgart, D-70469, Germany (04) :529-540
[17]   A CONCISE TOTAL SYNTHESIS OF THE AGLYCONE OF THE GILVOCARCINS [J].
DESHPANDE, PP ;
MARTIN, OR .
TETRAHEDRON LETTERS, 1990, 31 (44) :6313-6316
[18]   Transition metal catalyzed oxidative functionalization of carbon-hydrogen bonds [J].
Dick, AR ;
Sanford, MS .
TETRAHEDRON, 2006, 62 (11) :2439-2463
[19]   C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].
Dwight, Timothy A. ;
Rue, Nicholas R. ;
Charyk, Dagmara ;
Josselyn, Ryan ;
DeBoef, Brenton .
ORGANIC LETTERS, 2007, 9 (16) :3137-3139
[20]  
Dyker G, 2005, HANDBOOK OF C-H TRANSFORMATIONS: APPLICATIONS IN ORGANIC SYNTHESIS, VOL 1, pV