Palladium Catalyzed Stereoselective Hydrodehalogenation of Alkenyl Halides with Tributyltin Hydride
- 1 August 1991
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 64 (8), 2593-2595
- https://doi.org/10.1246/bcsj.64.2593
Abstract
The reduction of alkenyl halides with tributyltin hydride in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium has been studied. Alkenyl iodides reacted easily with tributyltin hydride at 25°C to give the corresponding hydrocarbons stereoselectively. However, the reaction of alkenyl bromides were sluggish at 25°C and needed heating at 75°C to complete.Keywords
This publication has 14 references indexed in Scilit:
- Triethylborane-Induced Hydrodehalogenation of Organic Halides by Tin HydridesBulletin of the Chemical Society of Japan, 1989
- Ultrasounds in Synthetic Reactions. III. Reduction of Organic Halides with Nickel(II) Chloride–Zinc–WaterBulletin of the Chemical Society of Japan, 1985
- Palladium-catalyzed coupling of vinyl triflates with organostannanes. A short synthesis of pleraplysillin-1Journal of the American Chemical Society, 1984
- Direct conversion of organic halides to aldehydes with carbon monoxide and tin hydride catalyzed by palladiumJournal of the American Chemical Society, 1983
- Palladium hydrides in organic synthesis. Reduction of aryl halides by sodium methoxide catalyzed by tetrakis(triphenylphosphine)palladiumThe Journal of Organic Chemistry, 1978
- Palladium catalyzed reductions of halo- and nitroaromatic compounds with triethylammonium formateThe Journal of Organic Chemistry, 1977
- Catalyse par manganese(II) : II. Reduction des halogenures vinyliques et aryliques par les organomagnesiens en presence de manganese(II)Journal of Organometallic Chemistry, 1976
- Organometallic compounds of Group III. XXXV. The stereospecific reductive alkylation of acetylenes by successive hydralumination and carbodemetalationThe Journal of Organic Chemistry, 1976
- Stereospecific 1,2-Dialkylvinylsilane synthesis via reductive alkylation of trialkylsilylacetyleneThe Journal of Organic Chemistry, 1976
- Novel method for the synthesis of isomerically pure vinyl halides from alkynes via the hydroalumination reactionJournal of the American Chemical Society, 1967