The Palladium Catalyzed Nucleophilic Substitution of Aryl Halides by Thiolate Anions
- 1 May 1980
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 53 (5) , 1385-1389
- https://doi.org/10.1246/bcsj.53.1385
Abstract
In the presence of a catalytic amount of tetrakis(triphenylphosphine) palladium, phenyl and methyl or methoxyphenyl iodides and bromides were found to react with thiolate anions in alcoholic solvents, to give the corresponding aryl sulfides in excellent yield. The reaction is useful to prepare symmetrical or unsymmetrical diaryl sulfides and aryl alkyl sulfides. The reaction mechanism does not involve aryl halide radical anions, but is thought to involve oxidative addition of aryl halide to Pd(0), nucleophilic substitution on the adduct followed by reductive elimination.This publication has 17 references indexed in Scilit:
- Palladium-catalyzed synthesis of 2-quinolone derivatives from 2-iodoanilinesThe Journal of Organic Chemistry, 1978
- Palladium-catalyzed vinylic substitution reactions with heterocyclic bromidesThe Journal of Organic Chemistry, 1978
- Palladium-catalyzed vinylic substitution reactions of N-vinyl amidesThe Journal of Organic Chemistry, 1978
- A general synthesis of terminal and internal arylalkynes by the palladium-catalyzed reaction of alkynylzinc reagents with aryl halidesThe Journal of Organic Chemistry, 1978
- A novel stereospecific alkenyl-alkenyl cross-coupling by a palladium- or nickel-catalyzed reaction of alkenylalanes with alkenyl halidesJournal of the American Chemical Society, 1976
- Nickel-Phosphine Complex-Catalyzed Grignard Coupling. I. Cross-Coupling of Alkyl, Aryl, and Alkenyl Grignard Reagents with Aryl and Alkenyl Halides: General Scope and LimitationsBulletin of the Chemical Society of Japan, 1976
- Palladium catalyzed synthesis of aryl, heterocyclic and vinylic acetylene derivativesJournal of Organometallic Chemistry, 1975
- Synthesis of aryl- and vinyl-substituted acetylene derivatives by the use of nickel and palladium complexesJournal of Organometallic Chemistry, 1975
- The remarkable reactivity of aryl halides with nucleophilesJournal of Chemical Education, 1974
- Selective carbon-carbon bond formation by cross-coupling of Grignard reagents with organic halides. Catalysis by nickel-phosphine complexesJournal of the American Chemical Society, 1972