Diels–Alder Reaction of Isobenzofurans/Cyclopentadienones with Tetrathiafulvalene: Preparation of Naphthalene, Fluoranthene, and Fluorenone Derivatives

Abstract

Diels-Alder reaction of 1,3-diarylbenzo[c]furan/cyclopentadienone with TTF followed by triflic acid mediated cleavage of the resulting adducts led to the formation of the respective 1,4-diaryl substituted naphthalenes, fluoranthenes, and fluorenones. The photophysical properties of representative diaryl-substituted hydrocarbons are also reported.

Chrysene‐Bridged Porphyrin Tweezers: Chiral Receptors for Fullerenes

“…Multistep reactions involving six thermally‐allowed pericyclic reactions (two Diels‐Alder reactions, two cheletropic reversions, retro‐Diels‐Alder reaction, and 1,5‐hydrogen shift) and one oxidation reaction must occur doubly in both NBD moieties of 1 . This proposed reaction pathway is strongly supported by detection of 7,10‐diphenylfluoranthene …”

Iridium-catalyzed reductive γ-lactonization of ortho-acylbenzoic acids in water: sustainable access to phthalides

“…9 Grignard addition followed by acidic treatment led to 1,3-diarylisobenzofurans with excellent optoelectronic properties. 1 g ,21 They can also be used as a precursor of the isobenzofuran intermediate under basic conditions, which underwent further cycloaddition to produce 8 . 22 In addition, thiolactone was also readily obtained via indium-catalyzed thiolation with (Me 3 Si) 2 S. 23 Our synthesis practically provided an abundance of phthalides with diverse functional groups, offering opportunities to produce structurally more complex and valuable derivatives via further structural modifications (Scheme 5b).…”

One‐Pot Access to Sulfonyl 2,3‐Diarylnaphthalenes via tBuOK‐Mediated Benzannulation of o‐Bis‐sulfonylmethyl Arenes with Diarylacetylenes

“…; [ 10b] (3) TfOH‐mediated Diels–Alder [4+2] cycloaddition of diarylisobenzofuran with tetrathiafulvalene, as explored by Mohanakrishnan et al . ; [10c] and (4) NiBr 2 (dppe)‐catalyzed Danheiser benzannulation of pyrazole‐conjugated iodoarene with 2 equivalents of alkynes, as discussed by Thavaselvan and Parthasarathy [10d] . Other annulation routes to Diels–Alder addition of vinyl/aryl glycals and arynes have been proven to synthesize diverse naphthalenes [10e–f] .…”