Vicinal Diamination of Arenes with Domino Aryne Precursors

Vicinal diamination of domino aryne precursors was achieved with sulfamides. The reaction proceeds through a two-aryne pathway, accepting two N-nucleophiles at the 1,2-positions of an arene ring. Symmetrical and unsymmetrical diaminobenzenes were readily obtained

Diamination of Domino Aryne Precursor with Sulfonamides

The reaction of a domino aryne precursor with sulfonamides efficiently afforded both 1,3-diaminobenzenes and trisubstituted 1,3-diaminobenzenes by simply varying the reaction conditions. Mechanistic study supports the sequential formation of two transient aryne intermediates involved in the reaction

Selective Aryne Formation via Grob Fragmentation from the [2+2] Cycloadducts of 3‑Triflyloxyarynes

A chemoselective ring-opening protocol of the formal [2+2] cycloadducts of 3-triflyloxyarynes was developed to generate 2,3-aryne intermediate via Grob fragmentation. A variety of 1,3-di- and 1,2,3-trisubstituted arenes could be readily accessed through this [2+2] cycloaddition-2,3-aryne formation sequence. The regioselectivity in these transformations originates from the steric repulsion of the aliphatic chain

Domino Aryne Precursor: Efficient Construction of 2,4-Disubstituted Benzothiazoles

An aryne precursor with a potential to perform domino aryne chemistry was proposed and synthesized. The reaction of this reagent with benzothioamide derivatives could afford 2,4-disubstituted benzothiazole with sequential incorporation of C–S, C–N, and C–C bonds on the consecutive three positions of the aryne precursor

Selective Aryne Formation via Grob Fragmentation from the [2+2] Cycloadducts of 3‑Triflyloxyarynes

A chemoselective ring-opening protocol of the formal [2+2] cycloadducts of 3-triflyloxyarynes was developed to generate 2,3-aryne intermediate via Grob fragmentation. A variety of 1,3-di- and 1,2,3-trisubstituted arenes could be readily accessed through this [2+2] cycloaddition-2,3-aryne formation sequence. The regioselectivity in these transformations originates from the steric repulsion of the aliphatic chain

Aryne 1,2,3-Trifunctionalization with Aryl Allyl Sulfoxides

An aryne 1,2,3-trisubstitution with aryl allyl sulfoxides is accomplished, featuring an incorporation of C–S, C–O, and C–C bonds on the consecutive positions of a benzene ring. The reaction condition is mild with broad substrate scope. Preliminary mechanistic study suggests a cascade formal [2 + 2] reaction of aryne with SO bond, an allyl S → O migration, and a Claisen rearrangement

Domino Aryne Annulation via a Nucleophilic–Ene Process

1,2-Benzdiyne equivalents possess the unique property that they can react with two aryno­philes through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic–ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope

Domino Aryne Annulation via a Nucleophilic–Ene Process

1,2-Benzdiyne equivalents possess the unique property that they can react with two aryno­philes through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic–ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope

Domino Aryne Annulation via a Nucleophilic–Ene Process

1,2-Benzdiyne equivalents possess the unique property that they can react with two aryno­philes through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic–ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope

Domino Aryne Annulation via a Nucleophilic–Ene Process

1,2-Benzdiyne equivalents possess the unique property that they can react with two aryno­philes through iteratively generated 1,2- and 2,3-aryne intermediates. Upon rational modification on the second leaving group of these aryne precursors, a domino aryne annulation approach was developed through a nucleophilic–ene reaction sequence. Various benzo-fused N-heterocyclic frameworks were achievable under transition metal-free conditions with a broad substrate scope