Thallium(III) in Organic Synthesis

被引:19
作者
Silva, Luiz F., Jr. [1 ]
Carneiro, Vania M. T. [1 ]
机构
[1] Univ Sao Paulo, Inst Quim, BR-05513970 Sao Paulo, Brazil
来源
SYNTHESIS-STUTTGART | 2010年 / 07期
基金
巴西圣保罗研究基金会;
关键词
thallium(III); rearrangement; coupling; cyclization; oxidation; MEDIATED RING CONTRACTION; DIASTEREOSELECTIVE TOTAL-SYNTHESIS; ETA(5)-CYCLOPENTADIENYL DERIVATIVES; OXIDATIVE REARRANGEMENT; HOMOALLYLIC ALCOHOLS; FACILE SYNTHESIS; ELECTROCHEMICAL PROPERTIES; ANTIBODY RECOGNITION; SECONDARY ANILINES; INDANS BEARING;
D O I
10.1055/s-0029-1218669
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This review article discusses the literature regarding thallium(III) compounds in synthetic organic chemistry published in the last decade, including several applications in the total synthesis of natural products. The reactions that received the most attention in this period were: i) the oxidative rearrangement of chalcones; ii) the ring contraction of cyclic alkenes; iii) the oxidation of homoallylic alcohols; iv) aromatic thallations; and v) oxidative couplings, including with phenols.
引用
收藏
页码:1059 / 1074
页数:16
相关论文
共 145 条
[31]   Ring Contraction of 1,2-Dihydronaphthalenes Promoted by Thallium(III) in Acetonitrile: A Diastereoselective Approach to Indanes [J].
Ferraz, Helena M. C. ;
Carneiro, Vania M. T. ;
Silva, Luiz F., Jr. .
SYNTHESIS-STUTTGART, 2009, (03) :385-388
[32]   A diastereoselective total synthesis of the sesquiterpene (±)-mutisianthol [J].
Ferraz, HMC ;
Aguilar, AM ;
Silva, LF .
TETRAHEDRON, 2003, 59 (31) :5817-5821
[33]  
Ferraz HMC, 2003, SYNTHESIS-STUTTGART, P1031
[34]  
Ferraz HMC, 2002, SYNTHESIS-STUTTGART, P1033
[35]   Thallium trinitrate mediated oxidation of 3-alkenols: Ring contraction vs cyclization [J].
Ferraz, HMC ;
Longo, LS ;
Zukerman-Schpector, J .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3518-3521
[36]   Construction of functionalized indans by thallium(III) promoted ring contraction of 3-alkenols [J].
Ferraz, HMC ;
Silva, LF .
TETRAHEDRON, 2001, 57 (50) :9939-9949
[37]   Thallium trinitrate mediated ring contraction of cis-2-decalones [J].
Ferraz, HMC ;
Silva, LF .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (04) :548-551
[38]   The reaction of 1-tetralones with thallium trinitrate supported on clay:: Ring contraction vs α-oxidation [J].
Ferraz, HMC ;
Silva, LF ;
Aguilar, AM ;
Vieira, TO .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2001, 12 (05) :680-684
[39]   Thallium trinitrate-mediated ring contraction of 1,2-dihydronaphthalenes: an approach to the synthesis of indans [J].
Ferraz, HMC ;
Silva, LF ;
Vieira, TO .
TETRAHEDRON, 2001, 57 (09) :1709-1713
[40]   CYCLIZATION OF UNSATURATED MONOTERPENIC ALCOHOLS MEDIATED BY THALLIUM-(III) SALTS [J].
FERRAZ, HMC ;
RIBEIRO, CMR ;
GRAZINI, MVA ;
BROCKSOM, TJ ;
BROCKSOM, U .
TETRAHEDRON LETTERS, 1994, 35 (10) :1497-1500