RT info:eu-repo/semantics/article
T1 Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions
A1 Feberero García, Claudia
A1 Virumbrales Ortiz, Cintia
A1 Sedano Labrador, Carlos
A1 Renedo Peña, Lorena
A1 Suárez Pantiga, Samuel
A1 Sanz Díez, Roberto
K1 o-Lithiation
K1 Carbamates
K1 Alkynylation
K1 Benzo[b]furans
K1 Cyclization
K1 Química
K1 Chemistry
AB A straightforward and transition metal-free one-pot protocol to synthesize halobenzo[b]furans has been developed employing simple and easily available starting materials such as O-aryl carbamates and alkynylsulfones. The fine-tuning of the different steps involved was key to achieving a successful one-pot procedure. Initially, a directed ortho-lithiation process, which uses the carbamate as the directed metalation group, was crucial in providing access to O-2-alkynylaryl N,N-diethyl carbamates by a direct alkynylation of the o-lithiated carbamate, with arylsulfonylalkynes as electrophilic reagents. Cyclization of the generated o-alkynylaryl carbamates was successfully accomplished through a strategy involving in situ carbamate alkaline hydrolysis under conventional heating or microwave irradiation, coupled with a subsequent heterocyclization step delivering the desired benzo[b]furans. A wide variety of new halobenzo[b]furans has been synthesized and their utility has been demonstrated by their further transformation.
PB MDPI
YR 2022
FD 2022-01
LK http://hdl.handle.net/10259/10507
UL http://hdl.handle.net/10259/10507
LA eng
NO This research was funded by the Ministerio de Ciencia e Innovación and FEDER (PID2020-115789GB-C21), and Junta de Castilla y León and FEDER (BU049P20). The project leading to these results has also received funding from “la Caixa” Foundation, under Agreement LCF/PR/PR18/51130007 > (CAIXA-UBU001). S.S.-P. and C.V. thank Junta de Castilla y León (Consejería de Educación) and Fondo Social Europeo (ESF+) for postdoctoral contracts. C.S. thanks Ministerio de Educación for a FPU predoctoral contract.
DS Repositorio Institucional de la Universidad de Burgos
RD 11-may-2026