2026-07-24T10:42:22Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/105072025-05-29T00:05:20Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Feberero García, Claudia 167 600 0000-0002-7105-9785 Virumbrales Ortiz, Cintia 578 600 0000-0003-0211-8988 Sedano Labrador, Carlos 780 600 0000-0002-9556-9667 Renedo Peña, Lorena 913 600 Suárez Pantiga, Samuel 544 600 0000-0002-4249-7807 Sanz Díez, Roberto 531 600 0000-0003-2830-0892 2025-05-28T07:39:34Z 2025-05-28T07:39:34Z 2022-01 http://hdl.handle.net/10259/10507 10.3390/molecules27020525 1420-3049 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. 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. application/pdf eng MDPI Molecules. 2022, V. 27, n. 2, p. 525-545 https://doi.org/10.3390/molecules27020525 Atribución 4.0 Internacional http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess o-Lithiation Carbamates Alkynylation Benzo[b]furans Cyclization Química Chemistry Transition Metal-Free Synthesis of Halobenzo[b]furans from O-Aryl Carbamates via o-Lithiation Reactions info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Molecules 27 2 525 545 THUMBNAIL Feberero-molecules_2022.pdf.jpg Feberero-molecules_2022.pdf.jpg IM Thumbnail image/jpeg 3482 https://riubu.ubu.es/bitstream/10259/10507/4/Feberero-molecules_2022.pdf.jpg f2ea6613d0f2d6d92f89094aac853345 MD5 4 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/10507/3/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 3 CC-LICENSE license_rdf license_rdf application/rdf+xml; charset=utf-8 908 https://riubu.ubu.es/bitstream/10259/10507/2/license_rdf 0175ea4a2d4caec4bbcc37e300941108 MD5 2 ORIGINAL Feberero-molecules_2022.pdf Feberero-molecules_2022.pdf application/pdf 1996938 https://riubu.ubu.es/bitstream/10259/10507/1/Feberero-molecules_2022.pdf c866bb84c8453cb3c77f3f941a2942b2 MD5 1 10259/10507 oai:riubu.ubu.es:10259/10507 2025-05-29 02:05:20.446 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es RWwgYXV0b3IgY29tbyDDum5pY28gdGl0dWxhciBkZSBsb3MgZGVyZWNob3MgZGUgcHJvcGllZGFkIGludGVsZWN0dWFsIGRlIGxhIG9icmEsIG8gZGlzcG9uaWVuZG8gZGUgbG9zIGRlYmlkb3MgcGVybWlzb3MgZGUgbG9zIG90cm9zIHRpdHVsYXJlcywgc2kgbG9zIGh1YmllcmEsIHkgZW4gdmlydHVkIGRlIGxvcyBkZXJlY2hvcyBxdWUgbGUgY29uZmllcmUgbGEgbGVnaXNsYWNpw7NuIHZpZ2VudGUgc29icmUgcHJvcGllZGFkIGludGVsZWN0dWFsIHkgZGVyZWNob3MgZGUgYXV0b3IsIA0KQVVUT1JJWkEgYSBsYSBVbml2ZXJzaWRhZCBkZSBCdXJnb3MgYSBkaWZ1bmRpciwgZGUgbWFuZXJhIGdyYXR1aXRhLCBlbCBjb250ZW5pZG8gZGUgbG9zIGFyY2hpdm9zIGRpZ2l0YWxlcyBxdWUgY29ycmVzcG9uZGVuIGFsIGRvY3VtZW50byBkZXNjcml0byBhbnRlcmlvcm1lbnRlLCBjb24gY2Fyw6FjdGVyIG5vIGV4Y2x1c2l2byB5IGRlIG1hbmVyYSBww7pibGljYSBlbiBhY2Nlc28gYWJpZXJ0byBhIHRyYXbDqXMgZGUgSW50ZXJuZXQsIHBhcmEgbG8gcXVlIGxhIEJpYmxpb3RlY2EgcHJvY2VkZXLDoSBhIGFyY2hpdmFybG9zIGVuIGVsIFJlcG9zaXRvcmlvIEluc3RpdHVjaW9uYWwuIEFzaW1pc21vIGF1dG9yaXphIGEgbGEgVW5pdmVyc2lkYWQgZGUgQnVyZ29zIGEgcmVhbGl6YXIgbGFzIHRyYW5zZm9ybWFjaW9uZXMgbmVjZXNhcmlhcyBkZSBmb3JtYXRvLCBubyBkZSBjb250ZW5pZG8sIHBhcmEgZ2FyYW50aXphciBsYSBwcmVzZXJ2YWNpw7NuIHkgZWwgYWNjZXNvIGVuIGVsIGZ1dHVyby4NCg0KRWwgYXV0b3IgZGlzcG9uZSwgZW4gdG9kbyBjYXNvLCBkZWwgZGVyZWNobyBhIHJldm9jYXIgZXN0YSBhdXRvcml6YWNpw7NuLg0KDQpMYSBjZXNpw7NuIGRlIGRlcmVjaG9zIGRlIGVzdGEgb2JyYSBzZSBlbmN1ZW50cmEgc3VqZXRhIGEgbGEgbGVnaXNsYWNpw7NuIHZpZ2VudGUgc29icmUgcHJvcGllZGFkIGludGVsZWN0dWFsIHkgZGVyZWNob3MgZGUgYXV0b3Iu