Visible light-induced hydrogen atom transfer trifluoromethylthiolation of aldehydes with bismuth catalyst
Jun Dong1, Zhuang Tang1, Luqian Zou1
1Key Laboratory of Chemistry in Ethnic Medicinal Resources, Yunnan Minzu University, Yuehua Street, Kunming, 650504, China. chenjingchao84@163.com.
Abstract:
By using a combination of BiCl3 and TBACl as a ligand-to-metal charge transfer (LMCT) photocatalyst, hydrogen atom transfer trifluoromethylthiolation of aldehydes was achieved under visible light irradiation. The present method provides economical and operationally simple access to trifluoromethylthioesters using low toxicity and cost-effective bismuth catalysts under mild reaction conditions. Based on the radical trapping experiments, the direct conversion of aldehydes to acyl radicals via chlorine radicals as HAT reagents was proposed as the reaction mechanism.
More Related Videos
Related Concept Videos
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
Hydroboration-Oxidation of Alkenes
Acid Halides to Alcohols: LiAlH4 Reduction
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Base-Promoted α-Halogenation of Aldehydes and Ketones


