Abstract
Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of terminal alkynes with sulfenyl chlorides is described. syn-Chlorothiolation offers a complementary synthetic route to chloroalkenyl sulfides. 2-Chloroalkenyl sulfides can easily be transformed into various sulfur-containing products, most of which are often found in natural products and pharmaceuticals.
| Original language | English |
|---|---|
| Pages (from-to) | 58-62 |
| Number of pages | 5 |
| Journal | Chemistry - An Asian Journal |
| Volume | 9 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Jan 2014 |
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Keywords
- addition
- alkynes
- chlorothiolation
- homogeneous catalysis
- palladium
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Palladium-catalyzed regio- and stereoselective chlorothiolation of terminal alkynes with sulfenyl chlorides. / Iwasaki, Masayuki; Fujii, Tomoya; Yamamoto, Arisa; Nakajima, Kiyohiko; Nishihara, Yasushi.
In: Chemistry - An Asian Journal, Vol. 9, No. 1, 01.2014, p. 58-62.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Palladium-catalyzed regio- and stereoselective chlorothiolation of terminal alkynes with sulfenyl chlorides
AU - Iwasaki, Masayuki
AU - Fujii, Tomoya
AU - Yamamoto, Arisa
AU - Nakajima, Kiyohiko
AU - Nishihara, Yasushi
PY - 2014/1
Y1 - 2014/1
N2 - Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of terminal alkynes with sulfenyl chlorides is described. syn-Chlorothiolation offers a complementary synthetic route to chloroalkenyl sulfides. 2-Chloroalkenyl sulfides can easily be transformed into various sulfur-containing products, most of which are often found in natural products and pharmaceuticals.
AB - Chlorothiolation of terminal alkynes with sulfenyl chlorides yields anti-adducts without transition-metal catalysts. In sharp contrast, transition-metal-catalyzed chlorothiolation has not been developed to date, possibly because organosulfur compounds can poison catalyst. Herein, the regio- and stereoselective palladium-catalyzed chlorothiolation of terminal alkynes with sulfenyl chlorides is described. syn-Chlorothiolation offers a complementary synthetic route to chloroalkenyl sulfides. 2-Chloroalkenyl sulfides can easily be transformed into various sulfur-containing products, most of which are often found in natural products and pharmaceuticals.
KW - addition
KW - alkynes
KW - chlorothiolation
KW - homogeneous catalysis
KW - palladium
UR - http://www.scopus.com/inward/record.url?scp=84890792796&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84890792796&partnerID=8YFLogxK
U2 - 10.1002/asia.201301295
DO - 10.1002/asia.201301295
M3 - Article
AN - SCOPUS:84890792796
VL - 9
SP - 58
EP - 62
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 1
ER -