Exploring Possible Surrogates for Kobayashi's Aryne Precursors

Autor(es)

Muraca, Ana Carolina A. ^[1] ; Raminelli, Cristiano ^[1]

Afiliação do(s) autor(es)

^[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ACS OMEGA; v. 5, n. 5, p. 2440-2457, FEB 11 2020.
• Citações Web of Science: 0

Resumo

A class of aryne precursors, that is, 2-(trimethylsilyl)aryl 4-chlorobenzenesulfonates, has been developed through well-established synthetic routes, which allow the formation of arynes under relatively mild conditions. All the aryne precursors were obtained from phenols and 4-chlorobenzenesulfonyl chloride, an inexpensive and easy-to-handle reagent with relatively low toxicity, and subjected to nucleophilic addition reactions, providing addition products in yields of 24 to 92%, and to cycloaddition reactions, affording cycloadducts in yields up to 80%. This work provides interesting insights into the mechanisms of aryne generation. In addition, 2-(trimethylsilyl)phenyl 4-chlorobenzenesulfonate was successfully employed in the total synthesis of (+/-)-aporphine. (AU)

• Processo FAPESP: 16/10894-7 - Desenvolvimento de novas rotas sintéticas visando à obtenção de precursores de arinos funcionalizados
• Beneficiário: Ana Carolina de Avelar Muraca
• Modalidade de apoio: Bolsas no Brasil - Doutorado
• Processo FAPESP: 17/21990-0 - 2-(Trialquilsilil)aril trifluorometanossulfonatos como precursores de arinos no desenvolvimento de metodologias para a obtenção de compostos heterocíclicos nitrogenados e sínteses totais de produtos naturais bioativos
• Beneficiário: Cristiano Raminelli
• Modalidade de apoio: Auxílio à Pesquisa - Regular