Intramolecular Hydroalkoxylation of Unactivated Alkenes Using Silane–Iodine Catalytic System

A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-,...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 15; pp. 3822 - 3825
Main Authors Fujita, Shoji, Abe, Masanori, Shibuya, Masatoshi, Yamamoto, Yoshihiko
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.08.2015
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ALCOHOLS
HYDROFUNCTIONALIZATION
CYCLIZATIONS
OLEFINS
HYDROGEN IODIDE
TRIFLIC ACID
HYDROAMINATION
ANNONACEOUS ACETOGENINS
HYDROETHERIFICATION
MARINE SPONGE
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Summary:A novel catalytic system using I2 and PhSiH3 for the intramolecular hydroalkoxylation of unactivated alkenes is described. NMR study indicated that in situ generated PhSiH2I is a possible active catalytic species. This catalytic system allows an efficient intramolecular hydroalkoxylation of phenyl-, trialkyl-, and 1,1-dialkyl-substituted alkenes as well as a variety of unactivated monoalkyl- and 1,2-dialkyl-substituted alkenes at room temperature. Mechanistic consideration based on significant experimental observations is also discussed.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01797