Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 21, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202200215
Keywords
Hydrosilanes; Nickel; Organosilanes; Silylation
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Funding
- National Natural Science Foundation of China [21772072, 22071084]
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We report a new method for synthesizing organohydrosilanes from phenols and ketones. This method involves unconventional Si-Cl cleavage and offers a complementary scope to established methods. It can successfully couple aryl- and alkenylhydrosilanes with various electrophiles, and is tolerant of different functional groups. The method has demonstrated gram-scale reactions, incorporation of organohydrosilanes into biologically active molecules, and derivatization of the formed products.
We report here a new method for the synthesis of organohydrosilanes from phenols and ketones. This method is established through reductive C-Si coupling of chlorohydrosilanes via unconventional Si-Cl cleavage. The reaction offers access to aryl- and alkenylhydrosilanes with a scope that is complementary to those of the established methods. Electron-rich, electron-poor, and ortho-/meta-/para-substituted (hetero)aryl electrophiles, as well as cyclic and acyclic alkenyl electrophiles, were coupled successfully. Functionalities, including Grignard-sensitive groups (e.g., primary amine, amide, phenol, ketone, ester, and free indole), acid-sensitive groups (e.g., ketal and THP protection), alkyl-Cl, pyridine, furan, thiophene, Ar-Bpin, and Ar-SiMe3, were tolerated. Gram-scale reaction, incorporation of -Si(H)R-2 into complex biologically active molecules, and derivatization of formed organohydrosilanes are demonstrated.
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