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Nickel-catalyzed thioallylation of alkynes with allyl phenyl sulfides.
Org Lett. 2007 Jan 18; 9(2):263-6.OL

Abstract

Allylic sulfides add to alkynes in the presence of nickel complexes efficiently to afford thio-1,4-dienes regio- and stereoselectively. Functional groups such as alkoxy, siloxy, hydroxy, carboalkoxy, chloro, and cyano groups are tolerated. A mechanism that involves a pi-allyl nickel intermediate is proposed on the basis of isolation of pi-allyl complexes and distribution of products in the reactions of alpha- or gamma-methylated allyl sulfide. [reaction: see text].

Authors+Show Affiliations

Department of Chemistry, Tsinghua University, Beijing 100084, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17217280

Citation

Hua, Ruimao, et al. "Nickel-catalyzed Thioallylation of Alkynes With Allyl Phenyl Sulfides." Organic Letters, vol. 9, no. 2, 2007, pp. 263-6.
Hua R, Takeda H, Onozawa SY, et al. Nickel-catalyzed thioallylation of alkynes with allyl phenyl sulfides. Org Lett. 2007;9(2):263-6.
Hua, R., Takeda, H., Onozawa, S. Y., Abe, Y., & Tanaka, M. (2007). Nickel-catalyzed thioallylation of alkynes with allyl phenyl sulfides. Organic Letters, 9(2), 263-6.
Hua R, et al. Nickel-catalyzed Thioallylation of Alkynes With Allyl Phenyl Sulfides. Org Lett. 2007 Jan 18;9(2):263-6. PubMed PMID: 17217280.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-catalyzed thioallylation of alkynes with allyl phenyl sulfides. AU - Hua,Ruimao, AU - Takeda,Hideaki, AU - Onozawa,Shun-ya, AU - Abe,Yoshimoto, AU - Tanaka,Masato, PY - 2007/1/16/pubmed PY - 2007/3/21/medline PY - 2007/1/16/entrez SP - 263 EP - 6 JF - Organic letters JO - Org Lett VL - 9 IS - 2 N2 - Allylic sulfides add to alkynes in the presence of nickel complexes efficiently to afford thio-1,4-dienes regio- and stereoselectively. Functional groups such as alkoxy, siloxy, hydroxy, carboalkoxy, chloro, and cyano groups are tolerated. A mechanism that involves a pi-allyl nickel intermediate is proposed on the basis of isolation of pi-allyl complexes and distribution of products in the reactions of alpha- or gamma-methylated allyl sulfide. [reaction: see text]. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17217280/Nickel_catalyzed_thioallylation_of_alkynes_with_allyl_phenyl_sulfides_ L2 - https://doi.org/10.1021/ol062686r DB - PRIME DP - Unbound Medicine ER -