Rhodium‐Catalyzed Directing‐Group‐Assisted Aldehydic C–H Arylations with Aryl Halides

• Published in: European journal of organic chemistry Vol. 2017; no. 34; pp. 5080 - 5093
• Main Authors: Rao, Maddali L. N., Ramakrishna, Boddu S.
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 15-09-2017
• Subjects: Aldehydes; Aromatic compounds; Aryl halides; Catalysis; C‐H activation; Halides; Rhodium
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201700881

A rhodium‐catalyzed general protocol for the directing‐group‐assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy‐ or amino‐group‐directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2‐hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo‐ and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3‐salicyloylpyridines in high yields.
A broad scope for the synthesis of 2′‐substituted benzophenones was established involving directing group (OH or NHTs) assisted C–H arylation of aryl aldehydes with aryl halides under rhodium‐catalyzed conditions.