Calcium-Catalyzed Bis-hydrothiolation of Unactivated Alkynes Providing Dithioacetals

Bis-hydrothiolation of alkynes providing anti-Markovnikov dithioacetals is reported. Lewis-acidic Ca(OSO2C4F9)2 (Ca(ONf)2) was synthesized for the first time and was shown to be an excellent catalyst for the transformation. The reaction is highly selective and has a wide substrate scope. It was reve...

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Bibliographic Details
Published inOrganometallics Vol. 33; no. 20; pp. 5626 - 5629
Main Authors Hut’ka, Martin, Tsubogo, Tetsu, Kobayashi, Shu̅
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 27.10.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Inorganic & Nuclear
Chemistry, Organic
Physical Sciences
Science & Technology
TRANSFORMATION
ACID
ASYMMETRIC 1,4-ADDITION
CHEMISTRY
CARBONYL-COMPOUNDS
BOND
SELECTIVE FORMATION
THIOACETALS
EFFICIENT
CYCLIZATION
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Summary:Bis-hydrothiolation of alkynes providing anti-Markovnikov dithioacetals is reported. Lewis-acidic Ca(OSO2C4F9)2 (Ca(ONf)2) was synthesized for the first time and was shown to be an excellent catalyst for the transformation. The reaction is highly selective and has a wide substrate scope. It was revealed that vinyl sulfides were intermediates for this transformation and that Ca(ONf)2 efficiently catalyzed the unprecedented reactions of unactivated vinyl sulfides with thiols to afford the dithioacetals in good to high yields.
ISSN:0276-7333
1520-6041
DOI:10.1021/om500442u