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, Junghoon; CHO, 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.
- Keywords
- Boron; Catalysis; Enantioselectivity; Esters; Palladium; Phosphorus compounds; Silicon; Sodium Iodide; C-C bond forming reaction; Cross-couplings; Palladium catalysis; Palladium-catalyzed; rev-Josiphos; Suzuki-Miyaura coupling; Suzuki-Miyaura cross-coupling; Synthetic application; Iodine compounds
- 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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