Transition‐Metal Free, One Pot Synthesis of Selenoesters via Reaction of Alkyl Selenides and Acyl Chlorides

Author:

Duarte Juliana S.1,De Oliveira Sandynara A.1,Da Silva Emily C. O.2,De Jesus Andreia P. V.1,Vasconcelos Leonardo G.1,De Sousa Júnior Paulo T.1,Rafique Jamal34ORCID,Saba Sumbal4ORCID,Stein André L.1

Affiliation:

1. Laboratório Central Analítica Departamento de Química Universidade Federal de Mato Grosso – UFMT Boa Esperança 78060-900 Cuiabá MT Brazil

2. Faculdade de Engenharia Universidade Federal de Mato Grosso – UFMT Boa Esperança 78060-900 Cuiabá MT Brazil

3. Instituto de Química – INQUI Universidade Federal do Mato Grosso do Sul – UFMS 79074-460 Campo Grande MS Brazil

4. LabSO, Instituto de Química – IQ Universidade Federal de Goiás – UFG 74690-900 Goiânia GO Brazil

Abstract

AbstractHerein, we report a new and efficient method for the synthesis of selenoesters by a direct coupling reaction of alkyl selenides with acyl chlorides in ethanol under transition metal‐free conditions. This nucleophilic acyl substitution afforded selenoesters in good yields. Traditionally, synthesis of selenoesters involve the reaction of acyl chlorides with an organoselenium anions generated in situ through the reductive cleavage of previously prepared diselenides. Our one‐pot approach avoids the pre‐preparation of diselenides and operated in atom‐economical and environmentally friendly conditions. The synthetic utility of these selenoesters was studied using Se‐butyl benzoselenoate as substrate in a Sonogashira‐type cross‐coupling reaction.

Funder

Conselho Nacional de Desenvolvimento Científico e Tecnológico

Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

Fundação de Amparo à Pesquisa do Estado de Mato Grosso

Publisher

Wiley

Subject

Organic Chemistry

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