Premium
TIPS‐TTF as a Precursor of Low‐Symmetry TTF Derivatives: Steric Protection Strategy in the Regioselective CH Modification of TTF
Author(s) -
Ueno Ryota,
Fujino Daishi,
Yorimitsu Hideki,
Osuka Atsuhiro
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201300623
Subject(s) - steric effects , surface modification , regioselectivity , ring (chemistry) , chemistry , palladium , combinatorial chemistry , stereochemistry , catalysis , organic chemistry
Triisopropylsilyltetrathiafulvalene (TIPS‐TTF) has been devised as a promising platform for the synthesis of low‐symmetry TTF derivatives. The bulky TIPS group allows TIPS‐TTF to undergo palladium‐catalyzed direct diarylation as well as LDA‐mediated dilithiation exclusively on the roomier dithiole ring. Subsequent fluoride‐mediated protodesilylation provided vicinally difunctionalized TTF, which could undergo further functionalization.