Pd(ii)-catalyzed decarboxylative acylation of phenylacetamides with α-oxocarboxylic acids via C–H bond activation

Abstract

A palladium-catalyzed decarboxylative acylation of phenylacetamides with α-oxocarboxylic acids via C-H bond activation is described. This protocol provides efficient access to a range of ortho-acyl phenylacetamides, which can be easily converted to 3-isochromanone derivatives.

Supported Palladium Nanoparticles Catalyzed Ortho-Directed C–C Coupling Reaction via a Pd0/PdII/PdIV Catalytic Cycle

“…[1][2][3][4][5][6] During the past few years, significant advances have been made in the formation of C-C bonds via the direct functionalization of C-H bonds catalyzed by palladium. [7][8][9][10][11][12][13][14][15][16][17][18][19][20] The transition-metal-catalyzed direct aroylation of arenes bearing different directing groups (such as arylpyridines, benzamides, 2 acetophenone oximes and anilides) C-H bond represents a direct and promising approach to access ketones. [21][22][23][24][25][26][27][28][29][30][31] Many successful strategies involve Pd-catalyzed ortho-coupling reactions with C-H bonds through cyclopalladation of 2-phenylpyridine.…”

Palladium‐Catalyzed 2‐(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

“…Phenylacetic scaffold is featured in pharmaceuticals and other bioactive compounds . For its functionalization, numerous C–H activation‐based methods have been developed including arylation, alkenylation, alkylation, alkynylation, halogenation,[6b], [6f], acylation, deuteration, lactonization and acetoxylation. [6b], [7f], [13b], Generally, the acetoxylation of arylacetic acids cannot be performed without installation of an amide directing group (Scheme ).…”

β-Carboline-directed decarboxylative acylation of ortho-C(sp2)–H of the aryl ring of aryl(β-carbolin-1-yl)methanones with α-ketoacids under palladium catalysis

“…2 Later Ge et al reported the Pd-catalysed decarboxylative acylation of acetanilides and 2-aryl pyridines at the orthoposition of the phenyl ring with α-oxocarboxylic acids via ligand-assisted ortho-C(sp2)-H activation in the presence of an oxidant. 3 Subsequently different directing groups including azobenzenes, 4 azoxybenzenes, 5 carboxylic acids, 6 cyclic enamides, 7 O-methyl ketoximes, 8 O-phenyl carbamates, 9 phenylacetamides, 10 2-aryloxypyridines, 11 pyridine-N-oxides, 12 indolines, 13 thioethers, 14 N-nitroso anilines, 15 tetrahydroquinolines 16 and indoles 17 have been used for performing the acylation via ligand-assisted activation of the ortho-C(sp2)-H bond leading to formation of biaryl ketones with high regioselectivities under mild reaction conditions. β-Carboline, a privileged scaffold, is core unit of several natural alkaloids and bioactive compounds endowed with diverse pharmacological properties.…”

“…Hz, 1H),10.07 (d, J = 8.5 Hz, 1H), 11.11 (s, 1H) 13. C NMR (100 MHz, CDCl 3 ): δ (ppm) = 112.2, 116.0, 120.3, 121.5, 121.7, 126.2, 126.6, 128.9, 129.1, 129.2, 131.0, 131.6, 132.3, 132.8, 134.9, 136.0, 136.2, 137.9, 138.5, 140.9, 155.7, 158.6.…”