Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes.

Rapid access to substituted 2-naphthyne intermediates via the benzannulation of halogenated silylalkynes† †Electronic supplementary information (ESI) available: Synthetic procedures, characterization data, and DFT calculations. CCDC 1539450 and 1539451. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7sc01625e Click here for additional data file. Click here for additional data file.

Synthesis of Highly Substituted Quinolines via a Tandem Ynamide Benzannulation/Iodocyclization Strategy.

A two-stage "tandem strategy" for the regiocontrolled synthesis of very highly substituted quinolines is described. Benzannulation based on the reaction of cyclobutenones or diazo ketones with N-propargyl-substituted ynamides proceeds via a cascade of several pericyclic reactions to generate multiply substituted aniline derivatives. In the second stage of the tandem strategy, triflate derivativ...

Benzannulation via the reaction of ynamides and vinylketenes. application to the synthesis of highly substituted indoles.

A two-stage "tandem strategy" for the synthesis of indoles with a high level of substitution on the six-membered ring is described. Benzannulation based on the reaction of cyclobutenones with ynamides proceeds via a cascade of four pericyclic reactions to produce multiply substituted aniline derivatives in which the position ortho to the nitrogen can bear a wide range of functionalized substitu...

Batch and flow photochemical benzannulations based on the reaction of ynamides and diazo ketones. Application to the synthesis of polycyclic aromatic and heteroaromatic compounds.

Highly substituted polycyclic aromatic and heteroaromatic compounds are produced via a two-stage tandem benzannulation/cyclization strategy. The initial benzannulation step proceeds via a pericyclic cascade mechanism triggered by thermal or photochemical Wolff rearrangement of a diazo ketone. The photochemical process can be performed using a continuous flow reactor which facilitates carrying o...

Synthesis of gamma-halogenated ketones via the Ce(IV)-mediated oxidative coupling of cyclobutanols and inorganic halides.

A straightforward method for the synthesis of gamma-halo-substituted ketones formed via the CAN-initiated oxidative addition of halides to 1-substituted cyclobutanols has been developed. This method has short reaction times, and provides access to a range of bromo and iodo gamma-substituted ketones in good to excellent yields.