Nickel-catalyzed decarboxylative cross-coupling of indole-3-acetic acids with aryl bromides by convergent paired electrolysis

Abstract

Herein, nickel-catalyzed decarboxylative cross-coupling of indole-3-acetic acids with aryl bromides by convergent paired electrolysis was developed in an undivided cell. This protocol features good functional group tolerance, chemical redox agent-...

Electrocatalytic synthesis: an environmentally benign alternative for radical-mediated aryl/alkenyl C(sp2)–C(sp3) cross-coupling reactions

“…In 2022, Mei and co-workers reported an interesting decarboxylative C(sp 2 )-C(sp 3 ) cross-coupling strategy for the preparation of synthetically and biologically valuable indole derivatives by merging convergent paired electrolysis and nickel catalysis (Scheme 54). 85 More importantly, the use of sacrificial electrodes/agents could be avoided owing to the inherent nature of convergent paired electrolysis, greatly improving the viability of this strategy. Notably, this reaction did not proceed in the absence of the base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), suggesting that deprotonation of the indole-3-acetic acid component is crucial for anodic oxidative decarboxylation.…”

Decarboxylative Cross‐coupling Reaction between Aryl Carboxylic Acids using BF@Propyl/Tris/Pd as a Novel Catalyst

“…[11][12][13][14] As against the organometallic compounds, carboxylic acids have a high level of stability against air and water and are accessible at low costs. [15][16][17] Another significant advantage associated with the decarboxylative cross-coupling reactions is that they avoid using any strong base for transmetalation. Therefore, these reactions are tolerant to numerous functional groups.…”

Photoelectrochemical Asymmetric Catalysis Enables Direct and Enantioselective Decarboxylative Cyanation

“…While the use of other box ligands such as L2, L3, and L4 resulted in diminished enantioselectivity (entries 7− 9), good results were obtained by replacing Ce(OTf) 3 The scope of the photoelectrochemical decarboxylative cyanation reaction was next investigated (Figure 2). The phenyl ring tolerated substitution at the para position with OMe (3), SMe (4), Me (5), Ph (6), F (7), Cl (8), Br (9), ester (10), and boronic ester (11), at the meta position with OMe (12) and Cl (13), and the ortho position with Ph (14) and Cl (15 and 16). Note that compound 13 can be converted to antiobesity drug lorcaserin.…”

“…Despite the long history of electrochemical decarboxylation, the carbon radicals generated on the electrode tend to dimerize (known as Kolbe electrolysis) or undergo further electron transfer oxidation to carbocations (known as Hofer–Moest reaction) . The constant interest of chemists in decarboxylative transformations has led to the development of many decarboxylative reactions employing electrochemical, photochemical, and transition metal methods. − ,− Despite these significant progresses, the direct enantioselective decarboxylative transformations of carboxylic acids remain difficult and are limited to redox neutral reactions of amino acids. − On the other hand, there are several elegant reports in the past few years on the redox neutral or reductive asymmetric decarboxylative transformations of N -hydroxyphthalimide (NHPI) esters (Figure A). − Relevant to our work, Liu and co-workers have disclosed photocatalytic decarboxylative cyanation of NHPI esters to afford chiral nitriles (Figure B) . The latter nitrile products are versatile synthetic intermediates for a variety of functionalities, and their asymmetric synthesis has thus been actively pursued. − …”