Synthesis of Alkyl Halides from Aldehydes via Deformylative Halogenation

Author(s)

Liang, Shengzong ^[1] ; Kumon, Tatsuya ^[2] ; Angnes, Ricardo A. ^[3] ; Sanchez, Melissa ^[4] ; Xu, Bo ^[5] ; Hammond, Gerald B. ^[1]

Affiliation

^[1] Univ Louisville, Dept Chem, Louisville, KY 40292 - USA

^[2] Kyoto Inst Technol, Fac Mol Chem & Engn, Kyoto 6068585 - Japan

^[3] State Univ Campinas Unicamp, Chem Inst, CP 6154, BR-13083970 Campinas, SP - Brazil

^[4] Calif State Univ Fresno, 2555 East San Ramon Ave M-S SB70, Fresno, CA 93740 - USA

^[5] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Minist Educ, Key Lab Sci & Technol Ecotext, Shanghai 201620 - Peoples R China

• Document type: Journal article
• Source: ORGANIC LETTERS; v. 21, n. 10, p. 3848-3854, MAY 17 2019.
• Web of Science Citations: 1

Abstract

An unprecedented deformylative halogenation of aldehydes to alkyl halides is presented. Under oxidative conditions, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)-radical that coupled with a halogen radical that was generated from inexpensive and atom-economical halogen sources (NaBr, NaI, or HCl), to yield an alkyl halide. Because of the mild conditions, a wide range of functional groups were tolerated, and excellent site selectivity was achieved. (AU)

• FAPESP's process: 17/01779-2 - Powerful Partners: Ionic Promoters and the Enantioselective Heck-Matsuda Reaction
• Grantee: Ricardo Almir Angnes
• Support Opportunities: Scholarships abroad - Research Internship - Doctorate