Switchable C−H Alkylation of Aromatic Acids with Maleimides in Water: Carboxyl as a Diverse Directing Group. Issue 16 (27th May 2019)

• Record Type: Journal Article
• Authors: Pu, Fan; Liu, Zhong‐Wen; Zhang, Lin‐Yan; Fan, Juan; Shi, Xian‐Ying
• Is Part Of: ChemCatChem. Volume 11:Issue 16(2019)
• Page Start: 4116
• Page End: 4122
• Publication Date: 2019-05-27
• Subjects: on water reaction -- ruthenium -- conjugate addition; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201900444
• Languages: English
• ISSNs: 1867-3880

Abstract

Abstract: A ruthenium‐catalyzed protocol to access conjugate addition or decarboxylative conjugate addition of aromatic acids with maleimides has been developed. The reaction shows interesting chemoselectivity with different substituted benzoic acids. The reaction pathway of C−H alkylation is controlled by the intrinsic property of aromatic acids but not reaction conditions. Under almost the same reaction conditions, carboxyl can act as either a classical directing group or a traceless directing group, thereby generating two kinds of products, i. e., 2‐alkyl substituted benzoic acids and alkyl substituted benzenes. These two reactions proceeded under mild and redox‐neutral conditions in neat water under the atmosphere of air, and could be easily scaled up to grams. The decarboxylative conjugate addition, where carboxyl acts as a traceless directing group, can be realized without the addition of any ligand, silver or copper salt. Abstract : A kiss of ruthenium : A ruthenium‐catalyzed switchable reaction to obtain either a conjugate addition product or a decarboxylative conjugate addition product from easily accessible aromatic acids and maleimides. A variety of different aryl substituted succinimides were obtained in mild and redox‐neutral conditions, neat water, with simple methodology and easy scale‐up.