Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Journal of the American Chemical Society called Allene C(sp2)-H Activation and Alkenylation Catalyzed by Palladium, Author is Schreib, Benedikt S.; Son, Mina; Aouane, Francoise A.; Baik, Mu-Hyun; Carreira, Erick M., which mentions a compound: 39901-94-5, SMILESS is O=C(Cl)C1=NC=CC=C1.[H]Cl, Molecular C6H5Cl2NO, Related Products of 39901-94-5.
Herein, a Pd-catalyzed C-H alkenylation of electronically unbiased allenes e.g., N-(6-(triisopropylsilyl)hepta-4,5-dien-1-yl)picolinamide, affording penta-1,2,4-triene products e.g., I in up to 94% yield was reported. A picolinamide directing group enables the formation of putative allenyl-palladacycles, which subsequently participate in a turnover limiting Heck-type reaction with electron-deficient alkene RCH=CH2 (R = methoxycarbonyl, (benzyloxy)carbonyl, [(4-methyl-2-oxo-2H-chromen-7-yl)oxy]carbonyl, etc.) coupling partners. This mechanistic proposal is consistent with exptl. and computational investigations. Addnl., for the first time, the use of picolinamide N,O-acetals as readily removable auxiliaries for C-H activation reactions, allowing the efficient alkenylation of allenyl carbinol derivatives was reported. Successful removal of the directing groups without affecting the reactive penta-1,2,4-triene substructure of the products e.g., I was demonstrated.
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