Regioselective carbonylative heteroannulation of o-iodothiophenols with allenes and carbon monoxide catalyzed by a palladium complex:: A novel and efficient access to thiochroman-4-one derivatives

被引:82
作者
Xiao, WJ [1 ]
Alper, H [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/jo9913098
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The palladium-catalyzed carbonylative ring-forming reactions of 2-iodothiophenol, and the corresponding substituted derivatives, with allenes and carbon monoxide are described. The reactions afford thiochroman-4-ones in good to excellent isolated yields with quite high regioselectivity. The catalytic heteroannulation may involve regioselective addition of the sulfur moiety of the reactants on the more positive end of the allene, arylpalladium formation, CO insertion, subsequent intramolecular cyclization, and then reductive elimination. The regioselectivity is probably governed by electronic effects.
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页码:9646 / 9652
页数:7
相关论文
共 79 条
[1]   DIOXIRANE OXIDATION OF (Z)-1-THIOAURONES, (E)-3-ARYLIDENE-1-THIOCHROMAN-4-ONES AND (E)-3-ARYLIDENE-1-THIOFLAVAN-4-ONES [J].
ADAM, W ;
GOLSCH, D ;
HADJIARAPOGLOU, L ;
LEVAI, A ;
NEMES, C ;
PATONAY, T .
TETRAHEDRON, 1994, 50 (46) :13113-13120
[2]   EVIDENCE OF THE FORMATION OF ZEROVALENT PALLADIUM FROM PD(OAC)2 AND TRIPHENYLPHOSPHINE [J].
AMATORE, C ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1992, 11 (09) :3009-3013
[3]   RATES AND MECHANISM OF THE FORMATION OF ZEROVALENT PALLADIUM COMPLEXES FROM MIXTURES OF PD(OAC)(2) AND TERTIARY PHOSPHINES AND THEIR REACTIVITY IN OXIDATIVE ADDITIONS [J].
AMATORE, C ;
CARRE, E ;
JUTAND, A ;
MBARKI, MA .
ORGANOMETALLICS, 1995, 14 (04) :1818-1826
[4]   PREPARATION OF BENZO[B]THIOPHENES BY PD(0)-CATALYZED INTRAMOLECULAR CYCLIZATION OF ALLYL (AND PROPARGYL) O-IODOPHENYL SULFIDES [J].
ARNAU, N ;
MORENOMANAS, M ;
PLEIXATS, R .
TETRAHEDRON, 1993, 49 (47) :11019-11028
[5]  
ARNOLDI A, 1984, SYNTHESIS-STUTTGART, P856
[6]   ABSOLUTE CONFIGURATION OF 1,2-CYCLONONADIENE AND CIS-3-ACETOXYCYCLONONENE [J].
BACH, RD ;
MAZUR, U ;
BRUMMEL, RN ;
LIN, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (25) :7120-&
[7]   Preparation of vinylogous 2-sulfonylindolines by the palladium-catalyzed cyclization of 1-sulfonyl-1,3-dienes with N-Cbz-o-iodoanilines [J].
Back, TG ;
Bethell, RJ .
TETRAHEDRON LETTERS, 1998, 39 (31) :5463-5464
[8]   PALLADIUM-CATALYZED CYCLIZATION-CYCLOPROPANATION AND CYCLIZATION - ANION CAPTURE PROCESSES OF VINYL TRIFLATES [J].
BROWN, A ;
GRIGG, R ;
RAVISHANKAR, T ;
THORNTONPETT, M .
TETRAHEDRON LETTERS, 1994, 35 (17) :2753-2756
[9]   Syntheses of indoles via a palladium-catalyzed annulation between iodoanilines and ketones [J].
Chen, CY ;
Lieberman, DR ;
Larsen, RD ;
Verhoeven, TR ;
Reider, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (09) :2676-2677
[10]   Synthesis of spiroisoindolinones by palladium-catalyzed heterocyclization of 2-iodobenzoyl chloride with ketimines [J].
Cho, CS ;
Wu, X ;
Jiang, LH ;
Shim, SC ;
Kim, HR .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1999, 36 (01) :297-300