Huanhuan Cui

Molecular Iodine-Mediated Difunctionalization of Alkenes with Nitriles and Thiols Leading to β-Acetamido Sulfides

A direct difunctionalization protocol of alkenes with nitriles and thiols toward β-acetamido sulfide derivatives has been proposed under metal-free synthesis conditions. The present protocol provides the facile and highly efficient synthesis of various β-acetamido sulfides in a scaled-up manner with good to excellent yields simply using inexpensive molecular iodine as a catalyst, DMSO as a mild oxidant, and readily available thiols as thiolating reagents.

Metal-free molecular iodine-catalyzed direct sulfonylation of pyrazolones with sodium sulfinates leading to sulfonated pyrazoles at room temperature

A simple and convenient molecular iodine-catalyzed direct sulfonylation of pyrazolones with sodium sulfinates has been developed in the presence of TBHP at room temperature. This methodology can allow for the synthesis of a series of valuable sulfonated pyrazoles in good to excellent yields simply using readily-available starting materials without requiring any metal or cryogenics.

Silver-catalyzed direct spirocyclization of alkynes with thiophenols: a simple and facile approach to 3-thioazaspiro[4,5]trienones

A new and convenient silver-catalyzed direct oxidative spirocyclization of alkynes with thiophenols is described. This methodology provides a simple and practical approach to various 3-thioazaspiro[4,5]trienones in moderate to good yields with high atom efficiency and excellent functional group tolerance.

Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant

A highly selective synthesis of sulfoxides from alkenes and thiols was established by visible-light photoredox catalysis at room temperature. This metal-free transformation protocol, which uses inexpensive Rose Bengal as the photocatalyst and air as the green oxidant, opens a new door toward the facile and practical construction of sulfoxides.

Metal-free direct construction of sulfenylated pyrazoles via the NaOH promoted sulfenylation of pyrazolones with aryl thiols

A convenient and cost-effective NaOH-promoted direct sulfenylation of pyrazolones with aryl thiols has been developed under mild and metal-free conditions. In this transformation, a range of valuable sulfenylated pyrazoles can be easily achieved in moderate to excellent yields, with high atom efficiency and good functional group tolerance.

Iodine-catalyzed Direct Thiolation of Indoles with Thiols Leading to 3-Thioindoles Using Air as the Oxidant

A simple and convenient method has been developed for the construction of 3-thioindoles via molecular iodine-catalyzed direct thiolation of indoles with thiols. The present protocol, which employs thiols as the thiolating agents, inexpensive molecular iodine as the catalyst, and environmentally benign air as the oxidant, allows the regioselective generation of 3-thioindoles in good to excellent yields.Graphical Abstract

Metal-free Oxidative Coupling of Aromatic Alkenes with Thiols Leading to (E)-Vinyl Sulfones

A facile I2O5-mediated direct oxidative coupling of aromatic alkenes with thiols toward vinyl sulfones has been developed under metal-free conditions. This methodology provides a convenient and efficient approach to various (E)-vinyl sulfones from readily available starting materials with excellent regioselectivity. The present oxidative coupling reaction, not only expands the scope of functionalization of alkenes with thiols, but also makes it a practical and powerful complement to traditional methods for the synthesis of (E)-vinyl sulfones.

Visible-light-enabled spirocyclization of alkynes leading to 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones

A mild and convenient visible-light-induced method has been developed for the construction of 3-sulfonyl and 3-sulfenyl azaspiro[4,5]trienones through metal-free difunctionalization of alkynes with sulfinic acids or thiols at room temperature. The present protocol simply utilizes visible light as the safe and eco-friendly energy source, and inexpensive and non-toxic organic dyes (Eosin Y and Na2-Eosin Y) as photocatalysts providing various sulfur-containing azaspiro[4,5]trienones in moderate to good yields.

NBS/DBU mediated one-pot synthesis of α-acyloxyketones from benzylic secondary alcohols and carboxylic acids

A simple and efficient one-pot NBS/DBU-mediated method has been developed for the synthesis of α-acyloxyketones from various benzylic secondary alcohols and carboxylic acids. Through this methodology, a series of α-acyloxyketones could be obtained in good to excellent yields under mild conditions. Importantly, this new reaction avoids the direct usage of toxic metal catalysts or potentially dangerous peroxide oxidants.

Visible-light-enabled oxyazidation of alkenes leading to α-azidoketones in air

A new and facile visible-light-enabled method for the synthesis of α-azidoketones has been developed via oxyazidation of alkenes with TMSN3 in air at room temperature. A series of α-azidoketones could be easily and efficiently obtained in moderate to excellent yields via cascade C–N and CO bond formation by simply using low-toxic and inexpensive Rose Bengal (1 mol%) and PhSeSePh (5 mol%) as co-catalysts.