Cobalt‐Catalyzed Selective Transformation of Levulinic Acid and Amines into Pyrrolidines and Pyrrolidinones using Hydrogen. Issue 16 (25th July 2022)

• Record Type: Journal Article
• Authors: Pan, Yixiao; Luo, Zhenli; Yang, Ji; Han, Jiahong; Yang, Jianbo; Yao, Zhen; Xu, Lijin; Wang, Peng; Shi, Qian
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 16(2022)
• Page Start: 2830
• Page End: 2836
• Publication Date: 2022-07-25
• Subjects: Amide -- Cobalt -- Hydrogenation -- Levulinic Acid -- Pyrrolidine -- Pyrrolidinone -- Reductive Amination; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200578
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Cobalt‐catalyzed selective transformation of levulinic acid and primary amines into pyrrolidines and pyrrolidinones under H2 has been developed. The catalyst system consisting of Co(NTf2 )2, 1, 1, 1‐tris(di(4‐methoxyphenyl)phosphinomethyl) ethane (( p ‐anisyl)triphos) and Me3 SiOTf works well for the synthesis of pyrrolidines via reductive amination/cyclization/deoxygenative reduction of amide, and using Co(NTf2 )2 /1, 1, 1‐tris(diphenylphosphinomethyl) ethane (triphos) as the catalyst under reduced hydrogen pressure results in exclusive formation of pyrrolidinones. Both aryl and alkyl primary amines are suitable substrates, and a variety of functional groups are tolerated. Meanwhile, 4‐oxo‐4‐arylbutanoic acids, 5‐oxohexanoic acid, 6‐oxoheptanoic acid, 2‐formylbenzoic acid, 2‐acetylbenzoic acid and 2′‐acetyl‐[1, 1′‐biphenyl]‐2‐carboxylic acid are also applicable, allowing for convenient access to cyclic amines and lactams with different ring size. Abstract :