Hypervalent iodine reagents have been developed as highly valuable reagents in synthetic organic chemistry during the past few decades. These reagents have been identified as key replacements of various toxic heavy metals in organic synthesis. Various synthetically and biologically important scaffolds have been developed using hypervalent iodine reagents either in stoichiometric or catalytic amounts. In addition, hypervalent iodine reagents have been employed for the synthesis of spirocyclic scaffolds via dearomatization processes. In this review, various approaches for the synthesis of spirocyclic scaffolds using hypervalent iodine reagents are covered including their stereoselective synthesis. Additionally, the applications of these reagents in natural product synthesis are also covered.
An alternative approach is described for the oxidation of organosulfides to the corresponding organosulfones by using trifluoromethyl 3-oxo-1λ3,2-benziodoxole-1(3H)-carboxylate as an oxidant. The oxidation of the sulfides was performed by using 2.4 equivalents of the oxidant in refluxing acetonitrile. The oxidation products were isolated in good to excellent yields.
An efficient metal-free approach for the synthesis of functionalized biaryl-cored diarylmethanes is described by the ring transformation of 2H-pyran-2-ones using 4-phenylbutan-2-one as carbanion source. Moreover, 2H-pyran-2-ones were reacted with 1,3-diphenylacetone in the presence of base to achieve functionalized teraryl-cored diarylmethanes. All the ring transformation reactions were performed under mild reaction conditions to afford the biaryl- and teraryl-cored reaction products in high yields.
Functionalized tetrahydroisoquinolines are convenient precursors for the construction of numerous heterocyclic compounds of therapeutic importance. In this paper we have illustrated an efficient synthesis of highly substituted tetrahydroisoquinolines from 2H-pyran-2-ones via nucleophile-mediated ring transformation with tert-butyl-4-oxopiperidine-1-carboxylate followed by acid-mediated cleavage of the tert-butyloxycarbonyl group. The products were achieved smoothly in high yields with flexibility of various substituents.
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