Palladium-Catalyzed Direct Addition of 2-Aminobenzonitriles to Sodium Arylsulfinates: Synthesis of o-Aminobenzophenones

The first example of the palladium-catalyzed synthesis of o-aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-aminobenzonitriles was reported. A plausible mechanism for the formation of o-aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-aminobenzophenones

Palladium-Catalyzed Direct Addition of 2-Aminobenzonitriles to Sodium Arylsulfinates: Synthesis of o-Aminobenzophenones

The first example of the palladium-catalyzed synthesis of o-aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-aminobenzonitriles was reported. A plausible mechanism for the formation of o-aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-aminobenzophenones

Efficient Approach to Carbinol Derivatives through Palladium-Catalyzed Base-Free Addition of Aryltriolborates to Aldehydes

Palladium-catalyzed base-free addition of aryltriolborates to aldehydes has been developed, leading to a wide range of carbinol derivatives in good to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The present synthetic route to carbinol derivatives could be readily scaled up to gram quantity without difficulty. Thus, this method represents a simple and practical procedure to access carbinol derivatives

Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(benzylidenamino)benzonitriles with arylboronic acids has been developed. This transformation features good functional group tolerance and provides an alternative synthetic pathway to access 2,4-diarylquinazolines in moderate to good yields. A plausible mechanism for the formation of 2,4-diarylquinazolines involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed

Unexpected Copper-Catalyzed Cascade Synthesis of Quinazoline Derivatives

The first example of a copper-catalyzed cascade reaction of (2-aminophenyl)­methanols with aldehydes using the combination of cerium nitrate hexahydrate and ammonium chloride has been developed, leading to a wide range of 2-substituted quinazolines in moderate to excellent yields. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of 2-substituted quinazoline derivatives

Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2‑Aryl-3-(arylamino)­quinazolinones: Synthesis of Fluorescent Indazolo­[3,2‑<i>b</i>]­quinazolinones

A palladium-catalyzed intramolecular aerobic oxidative C–H amination of 2-aryl-3-(arylamino)­quinazolinones has been developed, providing a variety of substituted indazolo­[3,2-<i>b</i>]­quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade “rollover” cyclometalation and C–H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials

Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2‑Aryl-3-(arylamino)­quinazolinones: Synthesis of Fluorescent Indazolo­[3,2‑<i>b</i>]­quinazolinones

A palladium-catalyzed intramolecular aerobic oxidative C–H amination of 2-aryl-3-(arylamino)­quinazolinones has been developed, providing a variety of substituted indazolo­[3,2-<i>b</i>]­quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade “rollover” cyclometalation and C–H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials