Rh-Catalyzed Domino Addition–Enolate Arylation: Generation of 3-Substituted Oxindoles via a Rh(lll) Intermediate

Abstract

A Rh-catalyzed domino conjugate addition-arylation sequence via a Rh(III) intermediate is reported. This process involving a proposed intramolecular oxidative addition of a rhodium enolate was utilized to achieve the synthesis of 3-substituted oxindole derivatives in moderate to excellent yields.

Selective synthesis of unsymmetric dibenzo[a,e]pentalenes by a rhodium-catalysed stitching reaction

“… 17 Finally, the intramolecular oxidative addition of bromoarene gives E and subsequent carbon–carbon bond-forming reductive elimination produces dibenzo[ a , e ]pentalene 3ba along with the regeneration of rhodium( i ) complex A . 18 Side-product 4ba is presumably formed through the insertion of 2a into the carbon–rhodium bond of B in the opposite regioselectivity, forming a carbon–carbon bond at the arylated carbon of 2a to give intermediate C′ . This then undergoes intramolecular alkyne insertion to give intermediate D′ , protonolysis of which leads to 4ba with the regeneration of rhodium( i ) complex A .…”

Rhodium‐Catalyzed Enantioselective Reductive Arylation: Convenient Access to 3,3‐Disubstituted Oxindoles

“…Our group recently reported a rhodium‐catalyzed 1,2‐diarylation of o ‐bromoaniline‐derived acrylamides for the synthesis of 3‐substituted oxindoles, using aryl boronic acids as the nucleophile (Scheme c) . Therein, a novel oxidative addition of the rhodium enolate was realized, and the cyclization was proposed to occur through a rhodium(III) intermediate.…”

Palladium-catalyzed allylation and deacylative allylation of 3-acetyl-2-oxindoles with allylic alcohols

“…procedure for the synthesis of 3-allyl-1methylindolin-2-one (3ab). 17 After performing the Pd-catalyzed allylation of compound 1a (see, Section 4.2), a solution of benzyltrimethylammonium hydroxide (Triton B) in MeOH (40 wt%, 136µL, 0.3 mmol) was added and, immediately, acetic acid (0.85 mL, 15 mmol). Immediately, the extractive work-up was performed with EtOAc (3x10 mL), the organic phases were washed with H2O (10 mL), dried with MgSO4, filtered and concentrated.…”