Iron-catalyzed carbonylative synthesis of tert-alkyl thioesters
Year: 2024
Type: article
Abstract: In the context of transition metal-catalyzed carbonylation reactions, iron-catalyzed carbonylative transformation retains considerable value due to its high abundance, affordability, and diverse catalytic modes. Among the carbonylation reactions, non-activated bulky alkyl halides and highly reactive thiol compounds are considered to be particularly challenging substrates. In this study, we studied the synthesis of various steric alkyl thioesters through the reaction of non-activated steric alkyl iodides with S -aryl thioester as the aryl sulfur source catalyzed by iron salt. This reaction offers a convenient approach for the synthesis of hindered thioesters. Preliminary mechanistic studies indicated the involvement of radical intermediates. In this study, we developed an iron-catalyzed carbonylative procedure for the synthesis of tert -alkyl thioesters. Various steric alkyl thioesters were produced in moderate to good yields from non-activated steric alkyl iodides by using S -aryl thioesters as the aryl sulfur sources. This reaction proceeded through radical intermediates and offers a convenient approach for the synthesis of hindered thioesters. • A new iron-catalyzed carbonylative coupling reaction. • A new procedure for steric alkyl thioesters synthesis. • Using S-aryl thioester as the aryl sulfur source without odor. • Iron catalyst activation of non-activated bulky alkyl halides.
Source: Green Synthesis and Catalysis
Authors: Sufang Shao, Zhi-Peng Bao, Xiao-Feng Wu
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: diamond
Award: G4833463889
OpenAlex ID: W4404516797