Efficient and Complementary Methods Offering Access to Synthetically Valuable 1,2-Dibromobenzenes

被引:31
作者
Diemer, Vincent [1 ]
Leroux, Frederic R. [1 ]
Colobert, Francoise [1 ]
机构
[1] Univ Strasbourg ECPM, CNRS, UMR 7509, F-67087 Strasbourg, France
关键词
Halogens; Metalation; Magnesium; Arynes; Arenes; Cross-coupling; FUSED POLYCYCLIC AROMATICS; FACILE N-ARYLATION; FUNCTIONALIZED ARYLMAGNESIUM; SELECTIVE SYNTHESIS; EXCHANGE-REACTION; O-ARYLATION; ARYNE; BENZYNE; CYCLOADDITION; DERIVATIVES;
D O I
10.1002/ejoc.201001217
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2-Dibromobenzenes are highly valuable precursors for various organic transformations, in particular, reactions based on the intermediate formation of benzynes. This report describes short sequences for the synthesis of various derivatives based on regioselective bromination, ortho-metalation, and halogen/metal permutations. 1,2-Dibromo-3-iodobenzene (2f), 1,2-dibromo-4-iodobenzene (4c), and 2,3-dibromo-1,4-diiodobenzene (5e) act as intermediates in these syntheses.
引用
收藏
页码:327 / 340
页数:14
相关论文
共 79 条
[1]   Hydrochloric acid catalysis of N-bromosuccinimide (NBS) mediated nuclear aromatic brominations in acetone [J].
Andersh, B ;
Murphy, DL ;
Olson, RJ .
SYNTHETIC COMMUNICATIONS, 2000, 30 (12) :2091-2098
[2]   INTERMOLECULAR BENZYNE CYCLOADDITION APPROACH TO APORPHINOIDS - TOTAL SYNTHESES OF NORCEPHARADIONE-B, CEPHARADIONE-B, DEHYDROANONAINE, DUGUENAINE, DEHYDRONORNUCIFERINE, PONTEVEDRINE, O-METHYLATHEROLINE, LYSICAMINE, AND ALKALOID PO-3 [J].
ATANES, N ;
CASTEDO, L ;
GUITIAN, E ;
SAA, C ;
SAA, JM ;
SUAU, R .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (09) :2984-2988
[3]   Heterosubstituted or functionalized derivatives of 1-and 2-(trifluoromethyl)naphthalenes emanating from aryne adducts [J].
Bailly, F ;
Cottet, F ;
Schlosser, M .
SYNTHESIS-STUTTGART, 2005, (05) :791-797
[4]   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
[5]  
Barluenga J, 2002, CHEM-EUR J, V8, P2034, DOI 10.1002/1521-3765(20020503)8:9<2034::AID-CHEM2034>3.0.CO
[6]  
2-I
[7]   Preparation and selective reactions of mixed bimetallic aromatic and heteroaromatic boron-magnesium reagents [J].
Baron, O ;
Knochel, P .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3133-3135
[8]  
BONNAFOUX L, 2008, THESIS U STRASBOURG
[9]   SPECTROPHOTOMETRIC STUDY OF TETRABUTYLAMMONIUM TRIBROMIDE [J].
BUCKLES, RE ;
POPOV, AI ;
ZELEZNY, WF ;
SMITH, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (10) :4525-4528
[10]   Concise Total Synthesis of (±)-cis-Trikentrin A and (±)-Herbindole A via Intermolecular Indole Aryne Cycloaddition [J].
Buszek, Keith R. ;
Brown, Neil ;
Luo, Diheng .
ORGANIC LETTERS, 2009, 11 (01) :201-204