Benzylation via Tandem Grignard reaction —iodotrimethylsilane (TMSI) mediated reduction

Autor:	Brian A. Roden, Mary K. Balmer, Darlene A. Cothron, Eric J. Stoner
Rok vydání:	1995
Předmět:	Reduction (complexity) chemistry.chemical_compound Tandem Chemistry Aryl Organic Chemistry Drug Discovery Grignard reaction Biochemistry Combinatorial chemistry
Zdroj:	Tetrahedron. 51:11043-11062
ISSN:	0040-4020
Popis:	A method has been developed which allows for the large scale preparation of biarylmethanes This method involves the initial formation of biarylmethanols via reaction of aryl Grignards with carbonyl compounds followed by a subsequent reduction with iodotrimethylsilane (TMSI). A number of improvements over existing literature procedures are reported as well as previously unobserved dimenzations. Studies reveal that as few as 3 equiv of TMSI will give complete reduction in most cases where either of the substituents are not heteroaromatic. Mono-substituted alkanols react with TMSI to afford the corresponding iodides. A mechanistic study of the TMSI reduction is also reported.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f781564a72349d5050830afdbeacd551 https://doi.org/10.1016/0040-4020(95)00659-v Zobrazit plný text záznamu Full Text from ScienceDirect