Metal- and base-free synthesis of aryl bromides from arylhydrazines. Issue 23 (4th June 2020)

• Record Type: Journal Article
• Authors: Phuc Tran, Dat; Nomoto, Akihiro; Mita, Soichiro; Dong, Chun-ping; Kodama, Shintaro; Mizuno, Takumi; Ogawa, Akiya
• Is Part Of: Tetrahedron letters. Volume 61:Issue 23(2020)
• Publication Date: 2020-06-04
• Subjects: Aryl bromide -- Arylhydrazine -- Metal-free -- Base-free; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2020.151959
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A metal- and base-free method to synthesize aryl bromides was developed. The use of CPME or THF as a co-solvent improved the bromination. Arylhydrazines with EWG is effectively converted to aryl bromides. Abstract: An efficient method was developed to synthesize brominated aromatic compounds from arylhydrazine hydrochlorides by using BBr3 in DMSO/CPME (cyclopentyl methyl ether) under air at 80 °C for 1 h without the use of bases or metal catalysts. In particular, this method could be carried out satisfactorily using electron-withdrawing groups to afford aryl bromides in a moderate to excellent yields.