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Beilstein J. Org. Chem. 2015, 11, 1112–1122, doi:10.3762/bjoc.11.125
Graphical Abstract
Figure 1: The sequential, reversible oxidation of TTF (1) to its stable radical cation (2) and dication (3) s...
Figure 2: Structures and possible substitution positions of MPTTFs (4) and BPTTFs (5).
Scheme 1: Large-scale synthesis of 6. Reagents and conditions: a) PhMe, reflux, 19 h, 74%; b) LiBr, NaBH4, TH...
Scheme 2: Preparation of 7. Reagents and conditions: a) TsCl, Et3N, DMAP, MeCN, rt → reflux, 3.5 h, 82%; b) (...
Scheme 3: Homo and cross-coupling reactions of 6 or 7 afford BPTTFs and MPTTFs, respectively. Reagents and co...
Scheme 4: Deprotection and methylation of cyanoethyl-protected thiol moieties on MPTTFs as reported by Jeppes...
Scheme 5: Deprotection and alkylation of cyanoethyl-protected thiol moieties on MPTTFs using CsOH·H2O or DBU....
Scheme 6: Deprotection and N-arylation of tosylated MPTTFs. Reagents and conditions: a) NaOMe, THF, MeOH, ref...
Scheme 7: Deprotection and N,N-diarylation of tosylated BPTTFs. Reagents and conditions: a) NaOMe, THF, MeOH,...