Direct Dehydroxylative Coupling Reaction of Alcohols with Organosilanes through Si–X Bond Activation by Halogen Bonding

The combined use of a halogen bond (XB) donor with trimethylsilyl halide was found to be an efficient cocatalytic system for the direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moder...

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Bibliographic Details
Published inOrganic letters Vol. 17; no. 12; pp. 3000 - 3003
Main Authors Saito, Masato, Tsuji, Nobuya, Kobayashi, Yusuke, Takemoto, Yoshiji
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.06.2015
Amer Chemical Soc
Subjects
Alcohols - chemistry
Chemistry
Chemistry, Organic
Halogens - chemistry
Hydrogen Bonding
Molecular Structure
Organosilicon Compounds - chemical synthesis
Organosilicon Compounds - chemistry
Physical Sciences
Science & Technology
Trimethylsilyl Compounds - chemical synthesis
Trimethylsilyl Compounds - chemistry
DIRECT ALLYLATION
REARRANGEMENT
LEWIS-ACID CATALYST
THERMODYNAMICS
BENZYLIC ALCOHOLS
NUCLEOPHILIC-SUBSTITUTION
COMPLEXES
ORGANOCATALYSIS
ALLYLSILANES
ALLYLTRIMETHYLSILANE
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Summary:The combined use of a halogen bond (XB) donor with trimethylsilyl halide was found to be an efficient cocatalytic system for the direct dehydroxylative coupling reaction of alcohol with various nucleophiles, such as allyltrimethylsilane and trimethylcyanide, to give the corresponding adduct in moderate to excellent yields. Detailed control experiments and mechanistic studies revealed that the XB interaction was crucial for the reaction. The application of this coupling reaction is also described.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.5b01290