Nickel(II) Chloride-Catalyzed Regioselective Hydrothiolation of Alkynes

Nickel(II) Chloride-Catalyzed Regioselective Hydrothiolation of Alkynes Full article

Journal

Advanced Synthesis & Catalysis
ISSN: 1615-4169 , E-ISSN: 1615-4150

Output data

Year: 2005, Volume: 347, Number: 15, Pages: 1993-2001 Pages count : 9 DOI: 10.1002/adsc.200505168

Authors

Ananikov Valentine P. ¹ , Malyshev Denis A. ¹ , Beletskaya Irina P. ² , Aleksandrov Grigory G. ³ , Eremenko Igor L. ³

Affiliations

1	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, Moscow 119991, Russia, Fax: (+7)-095-135-5328
2	Lomonosov Moscow State University, Chemistry Department, Vorob'evy gory, Moscow 119899, Russia, Fax: (+7)-095-939-3618
3	Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Prospect 31, Moscow 117907, Russia

Regioselective Markovnikov-type addition of PhSH to alkynes (HC≡C-R) has been performed using easily available nickel complexes. The non-catalytic side reaction leading to anti-Markovnikov products was suppressed by addition of γ-terpinene to the catalytic system. The other side reaction leading to the bis(phenylthio)alkene was avoided by excluding phosphine and phosphite ligands from the catalytic system. It was found that catalytic amounts of Et3N significantly increased the yield and selectivity of the catalytic reaction. Under optimized conditions high product yields of 60–85% were obtained for various alkynes [R=n-C5H11, CH2NMe2, CH2OMe, CH2SPh, C6H11(OH), (CH2)3CN]. The X-ray structure of one of the synthesized products is reported.

Ananikov V. , Malyshev D. , Beletskaya I. , Aleksandrov G. , Eremenko I.
Nickel(II) Chloride-Catalyzed Regioselective Hydrothiolation of Alkynes
Advanced Synthesis & Catalysis. 2005. V.347. N15. P.1993-2001. DOI: 10.1002/adsc.200505168 WOS Scopus OpenAlex

Web of science:	WOS:000234097100022
Scopus:	2-s2.0-29144490813
OpenAlex:	W2042281970

DB	Citing
OpenAlex	99
Scopus	104
Web of science	108