β-Bromoenol phosphate as a new precursor for the modular regioselective synthesis of substituted furans

Cu(ii)-catalyzed aerobic oxidative coupling of furans with indoles enables expeditious synthesis of indolyl–furans with blue fluorescence

“…π-Conjugated electron-rich systems represent valuable building blocks for the organic materials. 21 Various furan and thiophene containing conjugated molecules have been extensively studied for their materials properties. Hence, we decided to study the photophysical properties of these novel indole–furan–thiophene (IFT) analogs ( 3h , 3i , 3ak , 3al ) along with other representative indolyl–furans ( 3a , 3ae , 3s , 3t ) from our collection (Scheme 5).…”

Aerobic Catalytic Cross‐Dehydrogenative Coupling of Furans with Indoles Provides Access to Fluorophores with Large Stokes Shift

“…Based on the literature precedence, we surmised the possibility of the involvement of radical intermediates in cross‐coupling under Fe(III)/O 2 conditions [13b,17] . Hence, we performed the reaction in the presence of three radical scavengers – TEMPO, BHT and P(OEt) 3 (Scheme 5a).…”

Continuous isomerisation of 2,5‐dimethylfuran to 2,4‐dimethylfuran over Ga‐silicate

“…In a broader perspective the “importance of furans has attained a new dimension with its ever‐increasing use in materials science for a variety of vital applications such as conducting polymers, photovoltaics, self‐healing materials, etc. This importance has motivated chemists to constantly research new ways of synthesising furan derivatives with defined substitution patterns.” [5] Looking forward, furans are among the platform molecules considered for emerging biorefineries [6] . A readily available commercial technology for the transformation of furans is thus desirable.…”

“…The growing interest to use bio‐based polymers such as polyethylene furanoate (PEF), [7] or furan dicarboxylic acid as an alternative to (iso)terephtalic acid for the modification of PET, [8] or other polymer plastics directly from furan based rings constitute good examples. Hitherto, a few successful attempts using (catalytic) organic chemistry approaches for the synthesis of 2,4‐disubstituted furans have been presented [1,5,9–12] . The gold‐catalysed carbene transfer to alkynes [1] and annulation‐based β ‐bromoenol phosphate route, [5] as summarised in Scheme 1a) and b), respectively, provide access to a wide range of 2,4‐disubstituted furans.…”

“… Synthesis of 2,4‐dmf via a) Gold catalysed carbene transfer to alkynes [5] b) β ‐bromoenol phosphate route, [1] c) formose reaction and hydrogenation of 4‐hydroxymethylfuran [13] and d) isomerisation of 2,5‐dmf over zeolites/zeotypes (this work).…”