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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Exploring Possible Surrogates for Kobayashi's Aryne Precursors

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Muraca, Ana Carolina A. [1] ; Raminelli, Cristiano [1]
Total Authors: 2
[1] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema - Brazil
Total Affiliations: 1
Document type: Journal article
Source: ACS OMEGA; v. 5, n. 5, p. 2440-2457, FEB 11 2020.
Web of Science Citations: 0

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)

FAPESP's process: 16/10894-7 - Development of new synthetic routes in order to obtain functionalized aryne precursors
Grantee:Ana Carolina de Avelar Muraca
Support Opportunities: Scholarships in Brazil - Doctorate
FAPESP's process: 17/21990-0 - 2-(Trialkylsilyl)aryl trifluoromethanesulfonates as aryne precursors in the development of methodologies for obtaining nitrogen-containing heterocyclic compounds and total syntheses of bioactive natural products
Grantee:Cristiano Raminelli
Support Opportunities: Regular Research Grants