Regioselective Silylations of Propargyl and Allyl Pivalates through Ca-Promoted Reductive C(sp3)–O Bond Cleavage

A practical protocol for the regioselective preparation of 3-phenylpropargylsilanes and 3-phenylallylsilanes in yields of 36–77 and 48–86%, respectively, from readily accessible 3-phenylpropargyl and 1-phenylallyl pivalates was developed through reductive C­(sp3)–O bond cleavage. This method represe...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 23; no. 18; pp. 7129 - 7133
Main Authors Zhang, Tianyuan, Zheng, Suhua, Kobayashi, Taro, Maekawa, Hirofumi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 17.09.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CROSS-COUPLING REACTIONS
ETHERS
ALKYL
AMINO-ACIDS
STEREOCHEMISTRY
H BONDS
METAL
ALLYLSILANES
Online AccessGet full text

Cover

More Information
Summary:A practical protocol for the regioselective preparation of 3-phenylpropargylsilanes and 3-phenylallylsilanes in yields of 36–77 and 48–86%, respectively, from readily accessible 3-phenylpropargyl and 1-phenylallyl pivalates was developed through reductive C­(sp3)–O bond cleavage. This method represents the first example of the direct application of vastly abundant calcium granules to a reductive coupling reaction. A broad range of propargylsilanes and allylsilanes are simply prepared using easy-to-handle pivalates and chlorotrimethylsilane under mild catalyst-free and additive-free conditions.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02532