A new titanium tetrachloride mediated annulation of α-aryl-substituted carbonyl compounds with alkynes:: A simple and highly efficient method for the regioselective synthesis of polysubstituted naphthalene derivatives

被引：83
作者：
Kabalka, GW [1 ]
Ju, YH
Wu, ZZ
机构：
[1] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA
[2] Univ Tennessee, Dept Radiol, Knoxville, TN 37996 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 20期
关键词：
D O I：
10.1021/jo034330o
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new straightforward procedure has been developed for the synthesis of polysubstituted naphthalene derivatives. The reaction of a-aryl-substituted carbonyl compounds with terminal or internal alkynes in the presence of TiCl4 regioselectively generates substituted naphthalene derivatives in good to excellent yields.
引用
收藏
页码：7915 / 7917
页数：3
相关论文
共 37 条
[1]   FORMATION OF 6-MEMBERED AROMATIC RINGS BY CYCLIALKYLATION OF SOME ALDEHYDES AND KETONES [J].
BRADSHER, CK .
CHEMICAL REVIEWS, 1987, 87 (06) :1277-1297
[2]   Interaction modes of titanium tetrachloride with the carbonyl functionality [J].
Cozzi, PG ;
Solari, E ;
Floriani, C ;
ChiesiVilla, A ;
Rizzoli, C .
CHEMISCHE BERICHTE, 1996, 129 (11) :1361-1368
[3]   Tetraphosphine/palladium-catalysed Suzuki cross-coupling with sterically hindered aryl bromides and arylboronic acids [J].
Feuerstein, M ;
Doucet, H ;
Santelli, M .
TETRAHEDRON LETTERS, 2001, 42 (38) :6667-6670
[4]   Palladium-catalyzed (Ullmann-Type) homocoupling of aryl halides: A convenient and general synthesis of symmetrical biaryls via inter- and intramolecular coupling reactions [J].
Hennings, DD ;
Iwama, T ;
Rawal, VH .
ORGANIC LETTERS, 1999, 1 (08) :1205-1208
[5]   Synthesis of substituted naphthalenes by the palladium-catalyzed annulation of internal alkynes [J].
Huang, QH ;
Larock, RC .
ORGANIC LETTERS, 2002, 4 (15) :2505-2508
[6]   A novel titanium tetrahalide-mediated carbon-carbon bond-forming reaction:: Regioselective synthesis of substituted (E,Z)-1,5-dihalo-1,4-dienes [J].
Kabalka, GW ;
Wu, ZZ ;
Ju, YH .
ORGANIC LETTERS, 2002, 4 (20) :3415-3417
[7]   A new reaction of aryl aldehydes with aryl acetylenes in the presence of boron trihalides [J].
Kabalka, GW ;
Wu, ZZ ;
Ju, YH .
ORGANIC LETTERS, 2002, 4 (09) :1491-1493
[8]   Control of reactive site in palladium-catalyzed Grignard cross-coupling of arenes containing both bromide and triflate [J].
Kamikawa, T ;
Hayashi, T .
TETRAHEDRON LETTERS, 1997, 38 (40) :7087-7090
[9]  
Koning C. B., 2003, TETRAHEDRON, V59, P7
[10]   Synthesis of polycyclic aromatic hydrocarbons by the Pd-catalyzed annulation of alkynes [J].
Larock, RC ;
Doty, MJ ;
Tian, QP ;
Zenner, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (22) :7536-7537
1234