Palladium catalyzed reaction of 2-alkynylanilines with allyl chlorides. Formation of 3-allylindoles
作者： Koji Iritani , Seijiro Matsubara , Kiitiro Utimoto
DOI: 10.1016/S0040-4039(00)82047-X
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摘要: Abstract Pd(II) catalyzed reaction of N-carbomethoxy-2-alkynylanilines with allyl chlorides produces 2-alkyl-3-allyl-N-carbomethoxyindoles in the presence oxirances; Aminopalladation a N-carbomethoxy-2-alkynylaniline gives 3-(N-carbomethoxyindolyl)palladium intermediate, which regioselectively attacks on γ position to give 3-allyl-2-alkylindoles concurrent regeneration catalyst.
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sci-hub.se 参考文章(13)
Naoto. Yanagihara, Claude. Lambert, Koji. Iritani, Kiitiro. Utimoto, Hitosi. Nozaki, Palladium-catalyzed regio- and stereoselective cyclized coupling of lithium alkynoates with allyl halides Journal of the American Chemical Society. ,vol. 108, pp. 2753- 2754 ,(1986) , 10.1021/JA00270A043
Edward C. Taylor, Alan H. Katz, Hector Salgado-Zamora, Alexander McKillop, Thallium in organic synthesis. 68. A convenient synthesis of 2-phenylindoles from anilides Tetrahedron Letters. ,vol. 26, pp. 5963- 5966 ,(1985) , 10.1016/S0040-4039(00)98272-8
Junya Fujiwara, Yoshimi Fukutani, Hiromi Sano, Keiji Maruoka, Hisashi Yamamoto, Nucleophilic aromatic substitution by organoaluminum reagents. Application to the synthesis of indoles Journal of the American Chemical Society. ,vol. 105, pp. 7177- 7179 ,(1983) , 10.1021/JA00362A030
Koji Iritani, Naoto Yanagihara, Kiitiro Utimoto, Carboxylative coupling of propargylic alcohols with allyl chloride Journal of Organic Chemistry. ,vol. 51, pp. 5499- 5501 ,(1986) , 10.1021/JO00376A108
Yukio Wakabayashi, Yukitoshi Fukuda, Hiroshi Shiragami, Kiitiro Utimoto, Hitosi Nozaki, Preparation of furans from alkynols utilizing palladium catalyzed intramolecular addition of alcohol to acetylene as a key reaction Tetrahedron. ,vol. 41, pp. 3655- 3661 ,(1985) , 10.1016/S0040-4020(01)91384-5
C. E. Castro, E. J. Gaughan, D. C. Owsley, Indoles, Benzofurans, Phthalides, and Tolanes via Copper(I) Acetylides Journal of Organic Chemistry. ,vol. 31, pp. 4071- 4078 ,(1966) , 10.1021/JO01350A045
Claude Lambert, Kiitiro Utimoto, Hitosi Nozaki, Palladium(II) catalyzed cyclization of alkynoic acids Tetrahedron Letters. ,vol. 25, pp. 5323- 5326 ,(1984) , 10.1016/S0040-4039(01)81594-X
Edward G. Samsel, Jack R. Norton, MECHANISM OF ACETYLENE AND OLEFIN INSERTION INTO PALLADIUM-CARBON Σ BONDS Journal of the American Chemical Society. ,vol. 106, pp. 5505- 5512 ,(1984) , 10.1021/JA00331A019
Kiitiro Utimoto, Hiroshi Miwa, Hitosi Nozaki, Palladium-catalyzed synthesis of pyrroles Tetrahedron Letters. ,vol. 22, pp. 4277- 4278 ,(1981) , 10.1016/S0040-4039(01)82932-4
Barry M. Trost, New rules of selectivity: allylic alkylations catalyzed by palladium Accounts of Chemical Research. ,vol. 12, pp. 385- 393 ,(1980) , 10.1021/AR50155A001