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The catalytic indirect reductive quenching method is facilitated by a combination of Ir(III) photoredox and sulfide dual-catalysis system. This study demonstrated a method for synthesizing multi-substituted furans by using a photoredox/sulfide dual-catalysis system. This method enables the synthesis of various furan derivatives, including spirofurans and phthalans. The utility of this system was demonstrated through gram-scale synthesis of the pharmaceutical molecule talopram. Mechanistic studies and density functional theory calculations suggested the formation of sulfonium species via sulfide radical cations, followed by intramolecular cyclization to produce the desired furan derivatives., (© 2025 Wiley-VCH GmbH.)

The first synthesis of N -(acyloxy)ynamides was realized through the coupling of N -(acyloxy)amides and hypervalent alkynyliodane under mild conditions. This reaction probably involves biradical species ("C 2 ") generation and radical processes. Furthermore, we also demonstrated that N -(acyloxy)ynamide could be transformed into a N -sulfonylimidate derivative by a copper catalyst. This study provides new building blocks for synthetic organic chemistry reactions and improves understanding of the chemical reactivity of "C 2 ".

Sulfides and their derivatives are among the most important class of reagent in synthetic chemistry. Despite the importance of such compounds, the use of sulfide radical cations in synthetic chemistry is underdeveloped. To address this issue, herein, we describe alkene chlorotrifluoromethylation reactions promoted by photoredox/sulfide dual catalysis systems, which involves sulfide radical cations generated through the oxidation of sulfides by a photoredox catalyst. The high functional group tolerance of this chemistry was demonstrated using natural products and drug molecules as substrate alkenes.

A modular approach to underexplored, unsymmetrical [1]benzothieno[3,2- b ][1]benzothiophene (BTBT) scaffolds delivers a library of BTBT materials from readily available coupling partners by combining a transition-metal free Pummerer CH-CH-type cross-coupling and a Newman-Kwart reaction. This effective approach to unsymmetrical BTBT materials has allowed their properties to be studied. In particular, tuning the functional groups on the BTBT scaffold allows the solid-state assembly and molecular orbital energy levels to be modulated. Investigation of the charge transport properties of BTBT-containing small-molecule:polymer blends revealed the importance of molecular ordering during phase segregation and matching the highest occupied molecular orbital energy level with that of the semiconducting polymer binder, polyindacenodithiophene-benzothiadiazole (PIDTBT). The hole mobilities extracted from transistors fabricated using blends of PIDTBT with phenyl or methoxy functionalized unsymmetrical BTBTs were double those measured for devices fabricated using pristine PIDTBT. This study underscores the value of the synthetic methodology in providing a platform from which to study structure-property relationships in an underrepresented family of unsymmetrical BTBT molecular semiconductors., Competing Interests: There are no conflicts to declare., (This journal is © The Royal Society of Chemistry.)

Trifluoromethyl sulfoxides are a new class of trifluoromethylthiolating reagent. The sulfoxides engage in metal-free C-H trifluoromethylthiolation with a range of (hetero)arenes. The method is also applicable to the functionalization of important compound classes, such as ligand derivatives and polyaromatics, and in the late-stage trifluoromethylthiolation of medicines and agrochemicals. The isolation and characterization of a sulfonium salt intermediate supports an interrupted Pummerer reaction mechanism., (© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.)

Total synthesis of (+)-gliocladin C has been achieved on the basis of one-pot construction of the 3a-(3-indolyl)pyrroloindoline core structure by the cross-coupling of a tryptophan derivative and an indole promoted by a sulfonium species generated from dialkylsulfoxide and triflic anhydride.

An indole core bearing a functional group on the C2 position is often found as a key structure in biologically active natural products and pharmaceuticals. Here, we report direct C2-functionalization of indoles triggered by the formation of an iminium species generated from indole and a sulfonium reagent. The reaction proceeded under very mild conditions to give the corresponding C2-substituted indole derivatives in good to high yields., (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)

Arg-Gly-Asp (RGD) mimics were synthesized and their anti-platelet activity was evaluated. A concise method was developed for the synthesis of the target compounds from dehydroepiandrosterone and Wieland-Miescher and Hajos-Parrish ketones, which are suitable for readily available platform. Among the synthesized compounds, the perhydronaphthalene framework with a 3-(4-piperidinyl)propoxyl structure 3e possessed the highest anti-aggregative activity. The IC 50 values of 3e were 0.91 mM (ADP initiation) and 0.54 mM (collagen initiation).

The cross-coupling of tryptamine with substituted aniline to access C3a-nitrogen-linked pyrroloindolines has been developed via the consecutive cyclization of tryptamine with DMSO/Tf2O and the substitution of 3a-pyrroloindolylthionium intermediate with aniline. The use of 2,3-dihydrotryptamine instead of aniline enabled easy access to 3a-(1-indolyl)pyrroloindoline and the concise synthesis of C3a-N1'-linked pyrroloindoline alkaloid (±)-psychotriasine was accomplished.

The asymmetric total synthesis of (-)-leuconoxine has been achieved. The desymmetrization of a prochiral diester using a chiral phosphoric acid catalyst produced a highly enantioenriched lactam with excellent yield. The ring construction featuring an intramolecular N-acyliminium cyclization and the one-step pyrrolidone formation using Bestmann's ylide was successfully accomplished.

We report a one-pot procedure for forming a dimeric pyrroloindoline framework with a thionium reagent. The cyclization of tryptamine with DMSO and Tf(2)O, followed by substitution with indole derivatives, produced racemic 3a-indolylpyrroloindolines. The method enables rapid access to heterodimeric pyrroloindolines as well as to homodimeric pyrroloindolines.

Aliphatic C-H functionalization at indole 2α-position mediated by acyloxythionium species 1 generated from sulfoxide and acid anhydride has been developed. The combination of sulfoxide and TFAA with O-, N- and C-nucleophiles enabled introduction of various substituents in a one-pot procedure. Especially on utilizing DMSO, the combination provided a practical and efficient method for the synthesis of a wide range of 2α-substituted indoles.

A combination of dimethyl sulfoxide (DMSO) and trifluoroacetic anhydride (TFAA) mediates functionalization at the 2α-position of indole derivatives. Carbon and heteroatom nucleophiles were directly introduced via a one-pot procedure in excellent yields., (This journal is © The Royal Society of Chemistry 2011)