a,b-Alkenyl carboxylicacids undergo Cu II -mediated decarboxylative annulation reactions with aliphatic cyclic ketones to provides ynthetically valuable di-heterocycles.T he annulation process tolerates avariety of aliphatic ketones and heterocyclic alkenyl carboxylic acids,p roducing substituted fused furan derivatives with complete regioselectivity.T he current protocol offers as ynthetically applicable pathway to construct avariety of oligo-heterocycles through Cu-mediated single-electron transfer and decarboxylation. Notably,s ynthesis of relatively inaccessible di-heterocycles has been achieved successfully using this protocol.
An efficient method
has been developed to afford highly C-5 selective
olefination of thiazole derivatives utilizing a bifunctional template
in an intermolecular fashion. Coordinative interaction between the
substrates and the metal chelated template backbone plays a crucial
role in high C-5 selectivity. Excellent selectivity for the C-5 position
was observed while mono substituted (2- or 4-) or even more challenging
unsubstituted thiazoles were employed.
Achieving site-selective C-H functionalization of arene is a fundamental challenge, as it is mainly controlled by the electronic nature of the molecules. A chelation-assisted C-H functionalization strategy overcomes the selectivity issues by utilizing distance and geometry of covalently attached directing groups (DGs). This strategy requires stoichiometric DG installation/removal and a suitable functional group on which to tether the DG. Such strategies are ineffective for small heterocycles unless suitable functional groups are added. Moreover, heterocycles are not the judicious choice as substrates owing to the possibilities of catalyst deactivation. Inspired by recent developments, this work demonstrates the utilization of a chelating template backbone bearing covalently attached directing groups, which enables site-selective remote C-H functionalization of heterocycles. The observed selectivity is the outcome of non-covalent interactions between the heterocycles and bifunctional template backbone.
Aromatic heterocycles are important structural units in various naturally occurring compounds. Its abundance has drawn attention of synthetic chemists for decades. In the current scenario, new methodologies employing cheap transition metal reagents are highly desirable for efficient and practical synthesis of heterocyclic compounds. In this review article, strategies to synthesize aromatic heterocycles by inexpensive copper reagents have been discussed.
a,b-Alkenyl carboxylicacids undergo Cu II -mediated decarboxylative annulation reactions with aliphatic cyclic ketones to provides ynthetically valuable di-heterocycles.T he annulation process tolerates avariety of aliphatic ketones and heterocyclic alkenyl carboxylic acids,p roducing substituted fused furan derivatives with complete regioselectivity.T he current protocol offers as ynthetically applicable pathway to construct avariety of oligo-heterocycles through Cu-mediated single-electron transfer and decarboxylation. Notably,s ynthesis of relatively inaccessible di-heterocycles has been achieved successfully using this protocol.
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