Mechanism of Catalytic Addition of Benzeneselenol to Alkynes

Mechanism of Catalytic Addition of Benzeneselenol to Alkynes Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1608-3393 , E-ISSN: 1070-4280

Output data

Year: 2002, Volume: 38, Number: 10, Pages: 1475-1478 Pages count : 4 DOI: 10.1023/a:1022500420741

Authors

Ananikov V.P. ¹ , Malyshev D.A. ¹ , Beletskaya I.P. ²

Affiliations

1	Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russia
2	Faculty of Chemistry, Moscow State University, Vorob'evy gory, Moscow, Russia

Addition of benzeneselenol to terminal alkynes HCÍÄCR, catalyzed by Pd(0) complexes, leads to formation of mixtures of mono- and bis(phenylseleno)alkenes, depending on the nature of the R substituent. Electron-donor groups (R = Bu, CH2OH, CH2NMe2) give rise to addition according to the Markownikoff rule, whereas from alkynes with electron-acceptor groups (R = Ph, COOMe) mixtures of products are formed as a result of side reactions. A probable reaction mechanism includes oxidative addition of benzeneselenol to the metal, alkyne insertion into the PdÄSe bond, and reductive elimination.

Ananikov V.P. , Malyshev D.A. , Beletskaya I.P.
Mechanism of Catalytic Addition of Benzeneselenol to Alkynes
Russian Journal of Organic Chemistry. 2002. V.38. N10. P.1475-1478. DOI: 10.1023/a:1022500420741 WOS Scopus OpenAlex

Web of science:	WOS:000180431500011
Scopus:	2-s2.0-0036922613
OpenAlex:	W201265730

DB	Citing
OpenAlex	11
Scopus	10
Web of science	12