Synthesis of Silylbiaryl Triflates by Chemoselective Suzuki Reaction

Date
2017Author
Moreira, Barbara V. [UNIFESP]
Muraca, Ana Carolina A. [UNIFESP]
Raminelli, Cristiano [UNIFESP]
Type
ArtigoISSN
0039-7881Is part of
Synthesis-StuttgartDOI
10.1055/s-0036-1588332Metadata
Show full item recordAbstract
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.
Citation
Synthesis-Stuttgart. Stuttgart, v. 49, n. 5, p. 1093-1102, 2017.Keywords
iodinated silylaryl triflateschemoselective cross-coupling
Suzuki reaction
silylbiaryl triflates
benzyne chemistry
Sponsorship
Sao Paulo Research Foundation (FAPESP)FAPESP
Collections
- ICAQF - Artigos [1140]