Platinum(II)-catalyzed reaction of 2-alkynylbenzoates or benzothioates with vinyl ethers: A concise method for synthesis of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsuifanylnaphthalene derivatives

被引:96
作者
Kusama, H [1 ]
Funami, H [1 ]
Takaya, J [1 ]
Iwasawa, N [1 ]
机构
[1] Tokyo Inst Technol, Dept Chem, Meguro Ku, Tokyo 1528551, Japan
关键词
D O I
10.1021/ol0364024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise method for the preparation of 1-acyl-4-alkoxy- or 1-acyl-4-alkylsulfanyl naphthalenes has been developed by the reaction of o-ethynylbenzoates or benzothioates with vinyl ethers, in the presence of a catalytic amount of PtCl2. It is proposed that the reaction proceeds through [3 + 2]-cycloaddition of the platinum-containing carbonyl ylides followed by 1,2-alkyl migration.
引用
收藏
页码:605 / 608
页数:4
相关论文
共 32 条
[1]   RHODIUM ACETATE CATALYZES THE ADDITION OF CARBENOIDS ALPHA-OXYGENS TO ETHER OXYGENS [J].
ADAMS, J ;
POUPART, MA ;
GRENIER, L ;
SCHALLER, C ;
OUIMET, N ;
FRENETTE, R .
TETRAHEDRON LETTERS, 1989, 30 (14) :1749-1752
[2]   Functionalized 1,2-dihydronaphthalenes from the Cu(OTf)2-catalyzed [4+2] cycloaddition of o-alkynyl(oxo)benzenes with alkenes [J].
Asao, N ;
Kasahara, T ;
Yamamoto, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) :3504-3506
[3]   Lewis acid-catalyzed benzannulation via unprecedented [4+2] cycloaddition of o-alkynyl(oxo)benzenes and enynals with alkynes [J].
Asao, N ;
Nogami, T ;
Lee, S ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) :10921-10925
[4]   AuCl3-catalyzed benzannulation:: Synthesis of naphthyl ketone derivatives from o-alkynylbenzaldehydes with alkynes [J].
Asao, N ;
Takahashi, K ;
Lee, S ;
Kasahara, T ;
Yamamoto, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (43) :12650-12651
[5]   Selective transformations of phenylated diynes to polycyclic compounds by the RhCl3- and PtCl4-Aliquat 336(R) ion pair catalysts [J].
Baidossi, W ;
Schumann, H ;
Blum, J .
TETRAHEDRON, 1996, 52 (24) :8349-8364
[6]   Regioselective synthesis of substituted naphthalenes:: A novel de novo approach based on a metal-free protocol for stepwise cycloaddition of o-alkynylbenzaldehyde derivatives with either alkynes or alkenes [J].
Barluenga, J ;
Váquez-Villa, H ;
Ballesteros, A ;
González, JM .
ORGANIC LETTERS, 2003, 5 (22) :4121-4123
[7]   [FP-ETA-1-(1-POLYCYCLOALKYL)METHYLIDENE]+ TO [FP-ETA-2-(1-HOMOPOLYCYCLOALKENE)]+ REARRANGEMENT - CARBON MIGRATION IN IRON(II) ALKYLIDENES - A NEW ROUTE TO STABILIZED BRIDGEHEAD OLEFINS [J].
BLY, RS ;
BLY, RK ;
HOSSAIN, MM ;
LEBIODA, L ;
RAJA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (23) :7723-7730
[8]   Ru(II)- and Pt(II)-catalyzed cycloisomerization of ω-aryl-1-alkynes.: Generation of carbocationic species from alkynes and transition metal halides and its interception by an aromatic ring [J].
Chatani, N ;
Inoue, H ;
Ikeda, T ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (16) :4913-4918
[9]   PtCl2-catalyzed conversion of 1,6- and 1,7-enynes to 1-vinylcycloalkenes. Anomalous bond connection in skeletal reorganization of enynes [J].
Chatani, N ;
Furukawa, N ;
Sakurai, H ;
Murai, S .
ORGANOMETALLICS, 1996, 15 (03) :901-903
[10]   HIGHLY SELECTIVE SKELETAL REORGANIZATION OF 1,6-ENYNE AND 1,7-ENYNE TO 1-VINYLCYCLOALKENES CATALYZED BY [RUCL2(CO)(3)](2) [J].
CHATANI, N ;
MORIMOTO, T ;
MUTO, T ;
MURAI, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :6049-6050