Journal
ACS CATALYSIS
Volume 9, Issue 1, Pages 230-235Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b03979
Keywords
palladium catalysis; cross-coupling; enantioselectivity; rev-Josiphos; silicon; boron
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Funding
- Technology Development Program to Solve Climate Changes through the National Research Foundation (NRF) - Ministry of Science, ICT & Future Planning [NRF-2017M1A2A2049102]
- Cheongam Science Fellowship
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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.
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