One-Pot Rapid Access to Benzyl Silanes, Germanes, and Stannanes from Toluenes Mediated by a LiN(SiMe3)2/CsCl System

Organo-silanes, germanes, and stannanes are considered to be conducive to the development of cross-coupling reactions because they are stable, nontoxic, and easy to handle. Using feedstock toluenes, one-pot direct benzylic C–H silylations, germylations, and stannylations are developed. Simply combin...

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Published inJournal of organic chemistry Vol. 87; no. 21; pp. 13907 - 13918
Main Authors Yuan, Yaqi, Gu, Yuanyun, Wang, Yan-En, Zheng, Jiali, Ji, Jiaying, Xiong, Dan, Xue, Fei, Mao, Jianyou
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 04.11.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
METALATION
1,4-ADDITION REACTIONS
REAGENTS
HMDS
SI
SN
BOND
LITHIATION
CATALYZED SILYLATION
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Summary:Organo-silanes, germanes, and stannanes are considered to be conducive to the development of cross-coupling reactions because they are stable, nontoxic, and easy to handle. Using feedstock toluenes, one-pot direct benzylic C–H silylations, germylations, and stannylations are developed. Simply combining toluenes, LiN­(SiMe3)2/CsCl, and R3MCl (M = Si, Ge, Sn) generates a diverse array of bench-stable benzyl silanes, germanes, and stannanes (38 examples, 53–90% yields). The syntheses developed here are easy to access on scale.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01612