Herein it is shown, for the first time, that enolonium species are powerful electrophiles capable of reacting with aromatic compounds in an intermolecular manner to afford α-arylated ketones. The reaction compatible a variety functional groups, wide scope respect and ketone, even works polymerization-prone substrates such as substituted pyrroles, thiophenes, furans. Only 1.6 5 equiv commodity needed.

Enolonium species, resulting from the umpolung of ketone enolates by Koser's hypervalent iodine reagents activated boron trifluoride, react with a variety nitrogen heterocycles to form α-aminated ketones. The reactions are mild and complete in 4–5 h. Additionally, α-azidation enolonium species takes place using trimethylsilyl azide as convenient source nucleophile.

The intramolecular cycloaddition of o-quinone methides (o-QMs) with a carbonyl group has been envisaged and executed successfully in the context constructing complex rare [6,6,6,6]-tetracyclic core found integrastatins, epicoccolide A, epicocconigrone A. These transient o-QMs were generated easily from oxidative dearomatization corresponding C2-(aryl)benzofuran by employing Oxone acetone-water at rt. subsequent (or conjugated olefin) present on C2-aryl was spontaneous.

The first total synthesis of integrastatin B, a potent HIV-1 integrase inhibitor, has been accomplished in seven steps with 17.9% overall yield employing easily accessible starting compounds. Oxone-mediated oxidative benzofuran dearomatization cascade employed as the key skeletal construct to forge central tetracyclic nucleus.

Vinyl azides react with boron trifluoride activated Koser's hypervalent iodine reagent to afford azido-enolonium species. These previously unknown species efficiently aromatic compounds, allyltrimethylsilane, and azoles under mild conditions, no need for a transition-metal catalyst, forming C–C C–N bonds give variety of α-functionalized ketones. The intermediacy the proposed is supported by spectroscopic studies.

Indium trichloride catalyzes the reaction of vinyl azides with unfunctionalized indoles to give indoles. This is first example displacement azide group by a carbon nucleophile while preserving function. The protocol employs very mild conditions and offers excellent yields diverse 3-vinyl It amenable gram scale. Access library 3,3'-bis(indolyl)methanes through condensation 2 equiv an indole demonstrated.

Abstract The total synthesis of the putative structure xylarinol B is described and need to revise its demonstrated. central benzoxepine skeleton was constructed by employing a cobalt‐mediated bimolecular [2+2+2] Reppe–Vollhardt alkyne cycloaddition reaction.

Employing a cobalt-catalyzed [2 + 2 2] alkyne cyclotrimerization as the final step, short and efficient synthesis of cyclopropylallocolchicinoid its analogues having functional group variations at C9 and/or C10 C11 ring C has been accomplished.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTDecomposition of bicyclo[2.2.2]-1-formyl and pivaloyl peroxidesJ. E. Leffler A. MoreCite this: J. Am. Chem. Soc. 1972, 94, 7, 2483–2487Publication Date (Print):April 1, 1972Publication History Published online1 May 2002Published inissue 1 April 1972https://pubs.acs.org/doi/10.1021/ja00762a048https://doi.org/10.1021/ja00762a048research-articleACS PublicationsRequest reuse permissionsArticle Views203Altmetric-Citations14LEARN ABOUT THESE...

Herein, we report the Ag-catalyzed substrate-controlled interrupted radical pathways of iminyl radical. The benzylic groups played a crucial role in pathway selection involving series dimerization and hydrolysis, 1,5-H shift followed by cascade cyclization, direct N-(sp

Abstract The title reaction is efficiently used for the synthesis of cyclopropylallocolchicinoid (IIIa) and a range C9, C10 and/or C11 substituted analogues.