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Access to Enantioenriched Benzylic 1,1-Silylboronate Esters by Palladium-Catalyzed Enantiotopic-Group Selective Suzuki-Miyaura Coupling of (Diborylmethyl)silanes with Aryl Iodides

Title
Access to Enantioenriched Benzylic 1,1-Silylboronate Esters by Palladium-Catalyzed Enantiotopic-Group Selective Suzuki-Miyaura Coupling of (Diborylmethyl)silanes with Aryl Iodides
Authors
Kim, JunghoonCHO, SEUNG HWAN
POSTECH Authors
CHO, SEUNG HWAN
Date Issued
Jan-2019
Publisher
AMER CHEMICAL SOC
Abstract
This work describes the palladium-catalyzed enantiotopic-group selective Suzuki–Miyaura cross-coupling of (diborylmethyl)silanes with aryl iodides. The combination of a Pd(TFA)2 and rev-Josiphos-type ligand bearing a 3,5-bis(trifluoromethyl)phenyl as benzylic phosphine substituent in the presence of NaI as an additive and NaOMe as a base promotes the reaction to high efficiency and enantioselectivity. This method provides a convenient approach for synthesizing chiral benzylic 1,1-silylboronate esters from readily accessible reagents. Synthetic applications including stereospecific C–O, C–N, and C–C bond-forming reactions of boron group are also demonstrated.
This work describes the palladium-catalyzed enantiotopic-group selective Suzuki–Miyaura cross-coupling of (diborylmethyl)silanes with aryl iodides. The combination of a Pd(TFA)2 and rev-Josiphos-type ligand bearing a 3,5-bis(trifluoromethyl)phenyl as benzylic phosphine substituent in the presence of NaI as an additive and NaOMe as a base promotes the reaction to high efficiency and enantioselectivity. This method provides a convenient approach for synthesizing chiral benzylic 1,1-silylboronate esters from readily accessible reagents. Synthetic applications including stereospecific C–O, C–N, and C–C bond-forming reactions of boron group are also demonstrated.
This work describes the palladium-catalyzed enantiotopic-group selective Suzuki-Miyaura cross-coupling of (diborylmethyl)silanes with aryl iodides. The combination of a Pd(TFA)(2) and rev-Josiphos-type ligand bearing a 3,5-bis(trifluoromethyl)phenyl as benzylic phosphine substituent in the presence of NaI as an additive and NaOMe as a base promotes the reaction to high efficiency and enantioselectivity. This method provides a convenient approach for synthesizing chiral benzylic 1,1-silylboronate esters from readily accessible reagents. Synthetic applications including stereospecific C-O, C-N, and C-C bond-forming reactions of boron group are also demonstrated.
URI
http://oasis.postech.ac.kr/handle/2014.oak/94476
DOI
10.1021/acscatal.8b03979
ISSN
2155-5435
Article Type
Article
Citation
ACS CATALYSIS, vol. 9, no. 1, page. 230 - 235, 2019-01
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 CHO, SEUNG HWAN
Dept of Chemistry
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