Concise synthesis of functionalized benzocyclobutenones

Autor:	Nikolas A. Savage, Guangbin Dong, Peng-hao Chen
Rok vydání:	2014
Předmět:	Silylation Aryl Organic Chemistry Ketene Biochemistry Aryne Article Cycloaddition chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Dehydrohalogenation Organic chemistry
Zdroj:	Tetrahedron. 70:4135-4146
ISSN:	0040-4020
Popis:	A concise approach to access functionalized benzocyclobutenones from 3-halophenol derivatives is described. This modified synthesis employs a [2+2] cycloaddition between benzynes generated from dehydrohalogenation of aryl halides using LiTMP and acetaldehyde enolate generated from n-BuLi and THF, followed by oxidation of the benzocyclobutenol intermediates to provide benzocyclobutenones. The [2+2] reaction can be run on a 10-gram scale with an increased yield. A number of functional groups including alkenes and alkynes are tolerated. Coupling of benzynes with ketene silyl acetals to give 8-substituted benzocyclobutenones is also demonstrated.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::276b66e3b8d82d3d42542b2df39a9a05 https://doi.org/10.1016/j.tet.2014.03.080 Zobrazit plný text záznamu Full Text from ScienceDirect