Synthesis 2017; 49(05): 1093-1102
DOI: 10.1055/s-0036-1588332
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Silylbiaryl Triflates by Chemoselective Suzuki Reaction

Bárbara V. Moreira
Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Rua Prof. Artur Riedel, 275, Diadema, SP 09972-270, Brazil   eMail: raminelli@unifesp.br
,
Ana Carolina A. Muraca
Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Rua Prof. Artur Riedel, 275, Diadema, SP 09972-270, Brazil   eMail: raminelli@unifesp.br
,
Cristiano Raminelli*
Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Rua Prof. Artur Riedel, 275, Diadema, SP 09972-270, Brazil   eMail: raminelli@unifesp.br
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Publikationsverlauf

Received: 16. August 2016

Accepted after revision: 16. September 2016

Publikationsdatum:
19. Oktober 2016 (online)


Abstract

A modular approach for the synthesis of functionalized silylbiaryl triflates has been developed. Iodinated silylaryl triflates were prepared via a gram-scale diiodination reaction, followed by a one-flask transformation, in 42–52% overall yield. The iodinated silylaryl triflates were subjected to a novel chemoselective Suzuki reaction with arylboronic acids, using PdCl2(PPh3)2 as catalyst and K2CO3 as base in THF/H2O (1:1) at 80 °C for 24 hours, which afforded silylbiaryl triflates in 47–81% yield.

Supporting Information

 
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