Halogen-Lithium Exchange of Sensitive (Hetero)aromatic Halides under Barbier Conditions in a Continuous Flow Set-Up

Autor(es)

Weidmann, Niels ^[1] ; Nishimura, Rodolfo H. V. ^[2] ; Harenberg, Johannes H. ^[1] ; Knochel, Paul ^[1]

Afiliação do(s) autor(es)

^[1] Ludwig Maximilians Univ Munchen, Dept Chem, Butenandtstr 5-13, D-81377 Munich - Germany

^[2] Univ Fed Vale Sao Francisco, Colegiado Ciencias Farmaceut, Ave Jose de Sa Manicoba, BR-56304205 Petrolina, Petrolina - Brazil

• Tipo de documento: Artigo Científico
• Fonte: SYNTHESIS-STUTTGART; v. 53, n. 03 SEP 2020.
• Citações Web of Science: 0

Resumo

A halogen-lithium exchange reaction of (hetero)aromatic halides performed in the presence of various electrophiles such as aldehydes, ketones, Weinreb amides, and imines using BuLi as exchange reagent and a commercially available flow set-up is reported. The organolithiums generated in situ were instantaneously trapped with various electrophiles (Barbier conditions) resulting in the formation of polyfunctional (hetero)arenes. This method enables the functionalization of (hetero)arenes containing highly sensitive functional groups such as esters-, which are not tolerated in batch conditions. (AU)

• Processo FAPESP: 18/08856-5 - Metalações sobre condições de fluxo.
• Beneficiário: Rodolfo Hideki Vicente Nishimura
• Modalidade de apoio: Bolsas no Exterior - Estágio de Pesquisa - Doutorado