Palladium-Catalyzed Cross-Coupling of Monochlorosilanes and Grignard Reagents
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Using a palladium catalyst supported by DrewPhos, the alkylation of monochlorosilanes with primary and secondary alkylmagnesium halides is now possible. Arylation with sterically demanding aromatic magnesium halides is also enabled. This transformation overcomes the high bond strength of the Si–Cl bond (113 kcal/mol) and is a rare example of a transition-metal catalyzed process involving its activation. Because of the availability of both chlorosilanes and organomagnesium halide reagents, this method allows for the preparation of a wide range of alkyl and aryl silanes.
Keywords:alkylation / arylation / Grignard reagents / palladium / silane
Source:ACS Catalysis, 2017, 7, 12, 8113-8117
- American Chemical Society
- The University of Delaware, the National Science Foundation (CHE-1254360).
- The Delaware Economic 244 Development Office (Grant No. 16A00384).
- Gelest, Inc. 245 (Topper Grant Program).
- Research Corp. Cottrell 246 Scholars Program.
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3924
- This is the peer-reviewed version of the following article: Vulović, B.; Cinderella, A. P.; Watson, D. A. Palladium-Catalyzed Cross-Coupling of Monochlorosilanes and Grignard Reagents. ACS Catalysis 2017, 7 (12), 8113–8117. https://doi.org/10.1021/acscatal.7b03465