Shengzong Liang1, Tatsuya Kumon2, Ricardo A Angnes3, Melissa Sanchez4, Bo Xu5, Gerald B Hammond1. 1. Department of Chemistry , University of Louisville , Louisville , Kentucky 40292 , United States. 2. Faculty of Molecular Chemistry and Engineering , Kyoto Institute of Technology , Matsugasaki, Kyoto 606-8585 , Japan. 3. Chemistry Institute , State University of Campinas - Unicamp C.P . 6154, CEP.13083-970, Campinas , São Paulo , Brazil. 4. California State University Fresno , 2555 East San Ramon Avenue M/S SB70 , Fresno , California 93740 , United States. 5. Key Laboratory of Science and Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering and Biotechnology , Donghua University , Shanghai 201620 , China.
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.
An unprecedented deformylative halogenation of n class="Chemical">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.
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