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Rhodium-Catalyzed Selective C(sp2)-H Activation/Annulation of tert-Butyl Benzoyloxycarbamates with 1,3-Diynes: A One Step Access to Alkynylated Isocoumarins and Bis-Isocoumarins.

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We report here a Rh(III) catalyzed regio- and stereoselective synthesis of alkynylated and bis-isocoumarin from 1,3-dialkyne. Exclusive one-pot formation of 3,3-bis-isocoumarin isomers has been achieved by eliminating several other possibilities.… Click to show full abstract

We report here a Rh(III) catalyzed regio- and stereoselective synthesis of alkynylated and bis-isocoumarin from 1,3-dialkyne. Exclusive one-pot formation of 3,3-bis-isocoumarin isomers has been achieved by eliminating several other possibilities. This is the first example of transition metal catalyzed synthesis of alkynylated and bis-isocoumarin scaffolds. The protocol is compatible with a wide range of functional groups affording good to excellent yields. Several mechanistic investigations, including deuterium labeling experiments and kinetic isotope effect studies, have been carried out.

Keywords: bis isocoumarin; selective sp2; rhodium catalyzed; sp2 activation; activation annulation; catalyzed selective

Journal Title: Organic letters
Year Published: 2022

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