Iron Porphyrin Catalyzed Insertion Reaction of N‑Tosylhydrazone-Derived Carbenes into X–H (X = Si, Sn, Ge) Bonds

An efficient Fe­(TPP)­Cl catalyzed insertion reaction of in situ generated benzylic carbenes from N-tosylhydrazones into X–H (X = Si, Sn, Ge) was developed. Silanes bearing tertiary, secondary, and primary (3°, 2°, and 1°) Si–H bonds all reacted well to afford insertion products in moderate to high...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 20; no. 15; pp. 4641 - 4644
Main Authors Wang, En-Hui, Ping, Yuan-Ji, Li, Zong-Rui, Qin, Hongling, Xu, Zhen-Jiang, Che, Chi-Ming
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 03.08.2018
Amer Chemical Soc
Subjects
carbenes
catalytic activity
chemical bonding
chemical reactions
chemical structure
Chemistry
Chemistry, Organic
germanium
iron
microwave radiation
Physical Sciences
porphyrins
Science & Technology
silanes
silicon
tin
CARBON
REAGENTS
MECHANISM
SILICON
CONSTRUCTION
CYCLOPROPANATION
DIAZO-COMPOUNDS
SALTS
C-H
Online AccessGet full text

Cover

More Information
Summary:An efficient Fe­(TPP)­Cl catalyzed insertion reaction of in situ generated benzylic carbenes from N-tosylhydrazones into X–H (X = Si, Sn, Ge) was developed. Silanes bearing tertiary, secondary, and primary (3°, 2°, and 1°) Si–H bonds all reacted well to afford insertion products in moderate to high yields (up to 97%), and the reaction time could be significantly shortened to 1 h under microwave irradiation. A programmable stepwise double insertion strategy was developed for the synthesis of unsymmetrical tetrasubstituted silanes.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.8b01931