Copper‐Catalyzed C‐4 Carboxylation of 1‐Naphthylamide Derivatives with CBr₄/MeOH

Abstract

A simple and practical copper catalyzed C-4 carboxylation reaction of 1-naphthylamide derivatives using carbon tetra bromide and methanol is reported here. Picolinamide and its derivatives are used as a bidentate directing group for the distal C4-H functionalization. Various substituted naphthylamide derivatives, and anilides are employed for the carboxylation and proceeds in good yields under mild condition. From the outcome of experimental results, it is proposed that C4-H carboxylation reaction of 1-naphthylamides might proceed through a single electron transfer (SET) pathway.

Copper(i)-catalyzed radical carboamination reaction of 8-aminoquinoline-oriented buteneamides with chloroform: synthesis of-β-lactams

“…This may be due to the decomposition of trichloromethyl radicals into chlorine radicals and dichloromethyl carbene. Since Ghosh research group captured the tribromomethyl radical by using 2,6-di- tert -butyl-4-methylphenol (BHT) successfully, 27 we try to captured the trichloromethyl radical by using the same method. It's exciting to obtain the BHT trapped trichloromethyl radical compound 4 ( Scheme 3A ).…”

Regioselective C−H Functionalization of Naphthalenes: Reactivity and Mechanistic Insights

“…A similar strategy was employed by Ghosh's group to achieve a C4-carboxylation of naphthylamide 12 (Scheme 31). [54] As previously, a single electron transfer from Cu(II) complex to CBr 4 was proposed in order to achieve the carbon addition in C4 and thus introduce an ester group. The same group developed an extension of this reaction to 8-aminoquinoline derivatives but this time using visible light to promote the reaction with a ruthenium catalyst.…”

“…A similar strategy was employed by Ghosh's group to achieve a C4‐carboxylation of naphthylamide 12 (Scheme ) . As previously, a single electron transfer from Cu(II) complex to CBr 4 was proposed in order to achieve the carbon addition in C4 and thus introduce an ester group.…”

Silver(I) Promoted the C4–H Bond Phosphonation of 1-Naphthylamine Derivatives with H-Phosphonates

“…However, the development for para-selective C4–H functionalization is not very comprehensive. Until 2017, reports on the construction of C–S, C–N, C–O, C–C, and C–X (X = Br and I) bonds of 1-naphthylamine derivatives at the C4 site began to appear in our and several other groups. This chemistry process is mainly based on the bidentate chelation, single electron transfer (SET) between the reactive radical cation species, substitution of the radical intermediate with the 1-naphthylamine derivative at the C4 site, and dissociation from the metal atom (Scheme a).…”