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Development of new synthetic routes in order to obtain functionalized aryne precursors

Grant number: 16/10894-7
Support type:Scholarships in Brazil - Doctorate
Effective date (Start): August 01, 2016
Effective date (End): April 30, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry
Principal Investigator:Cristiano Raminelli
Grantee:Ana Carolina de Avelar Muraca
Home Institution: Instituto de Ciências Ambientais, Químicas e Farmacêuticas (ICAQF). Universidade Federal de São Paulo (UNIFESP). Campus Diadema. Diadema , SP, Brazil

Abstract

Benzyne chemistry has found applications in organic chemistry, including total syntheses of natural products and preparations of functional materials. In this sense, 2-(trimethylsilyl)aryl trifluoromethanesulfonates appear as an important alternative for the formation of benzyne and derivatives under mild reaction conditions. Accordingly, we intend to develop alternative routes for the synthesis of aryne precursors. Initially, we expect to produce 2-(trimethylsilyl)aryl 4-chlorobenzenesulfonates, which will arise as a new class of aryne precursors, employing a sequence of reactions well established, avoiding the use of trifluoromethanesulfonic anhydride, aiming to the formation of arynes under mild conditions. In the sequence, we intend to develop two routes for the synthesis of functionalized silylaryl benzenesulfonates, using palladium catalyst in the key step of the first, and photoredox cross-coupling, employing catalysts of nickel and iridium in the key step of the second. In addition, we expect to produce 2-(triethylsilyl)aryl 4-chlorobenzenesulfonates containing functional groups, through C-H bond activation, employing potassium tert-butoxide in catalytic amount at room temperature.