Metal‐Free Hydrogenation of N‐Heterocycles with Trimethylamine Borane and TFA in Aqueous Solution. Issue 21 (13th October 2022)

• Record Type: Journal Article
• Authors: Zeng, Yao‐Fu; Li, Yi‐Na; Zhou, Ming‐Xi; Han, Shuai; Guo, Yu; Wang, Zhen
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 21(2022)
• Page Start: 3664
• Page End: 3669
• Publication Date: 2022-10-13
• Subjects: metal-free -- hydrogenation -- trimethylamine borane -- aqueous solution -- trifluoroacetic acid; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200795
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A metal‐free hydrogenation of quinoxalines and indoles with Me3 N ⋅ BH3 and TFA in water at room temperature is reported. The protocol is featured with the usage of environmentally friendly water as the solvent, no need of metal catalyst and broad substrate scope. Sensitive functional groups such as OH‐, NH2 ‐, Cl‐, Br‐, especially ‐CN and ‐CO2 Me were well tolerated. Preliminary mechanistic studies suggested that TFA and Me3 N ⋅ BH3 provided the proton and hydride sources for the product, respectively. Abstract :