Synthesis of Silylbiaryl Triflates by Chemoselective Suzuki Reaction

Synthesis of Silylbiaryl Triflates by Chemoselective Suzuki Reaction

Author Moreira, Barbara V. Autor UNIFESP Google Scholar
Muraca, Ana Carolina A. Autor UNIFESP Google Scholar
Raminelli, Cristiano Autor UNIFESP Google Scholar
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 degrees C for 24 hours, which afforded silylbiaryl triflates in 47-81% yield.
Keywords iodinated silylaryl triflates
chemoselective cross-coupling
Suzuki reaction
silylbiaryl triflates
benzyne chemistry
xmlui.dri2xhtml.METS-1.0.item-coverage Stuttgart
Language English
Sponsor Sao Paulo Research Foundation (FAPESP)
Grant number FAPESP: 2015/09984-9
Date 2017
Published in Synthesis-Stuttgart. Stuttgart, v. 49, n. 5, p. 1093-1102, 2017.
ISSN 0039-7881 (Sherpa/Romeo, impact factor)
Publisher Georg Thieme Verlag Kg
Extent 1093-1102
Access rights Closed access
Type Article
Web of Science ID WOS:000398093000020

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