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5-endo cyclizations of NHC-boraallyl radicals bearing ester substituents : characterization of derived 1,2-oxaborole radicals and boralactones
Item metadata
dc.contributor.author | Dai, Wen | |
dc.contributor.author | McFadden, Timothy R. | |
dc.contributor.author | Curran, Dennis P. | |
dc.contributor.author | Früchtl, Herbert A. | |
dc.contributor.author | Walton, John C. | |
dc.date.accessioned | 2019-10-29T00:36:09Z | |
dc.date.available | 2019-10-29T00:36:09Z | |
dc.date.issued | 2018-11-21 | |
dc.identifier | 256781527 | |
dc.identifier | 8a558f4e-a4ed-4b04-b588-28a94bcd1b38 | |
dc.identifier | 85056802947 | |
dc.identifier | 30369236 | |
dc.identifier | 000451496800045 | |
dc.identifier.citation | Dai , W , McFadden , T R , Curran , D P , Früchtl , H A & Walton , J C 2018 , ' 5- endo cyclizations of NHC-boraallyl radicals bearing ester substituents : characterization of derived 1,2-oxaborole radicals and boralactones ' , Journal of the American Chemical Society , vol. 140 , no. 46 , pp. 15868-15875 . https://doi.org/10.1021/jacs.8b09288 | en |
dc.identifier.issn | 0002-7863 | |
dc.identifier.other | ORCID: /0000-0003-2746-6276/work/56638691 | |
dc.identifier.other | ORCID: /0000-0001-6647-4266/work/60887474 | |
dc.identifier.uri | https://hdl.handle.net/10023/18794 | |
dc.description | J.C.W. thanks EaStCHEM for financial support, and D.P.C. thanks the U.S. National Science Foundation. Computational support was provided through the EaStCHEM Research Computing Facility. | en |
dc.description.abstract | EPR studies of radical hydrogen abstraction reactions of N-heterocyclic carbene (NHC) complexes of alkenylboranes bearing two ester substituents revealed not the expected boraallyl radicals but instead isomeric 1,2-oaxborole radicals. Such radicals are new, and DFT calculations show that they arise from the initially formed boraallyl radicals by a rapid, exothermic 5-endo cyclization. These spectroscopic and computational discoveries prompted a series of preparative experiments that provided access to a novel family of robust NHC-boralactones. A one-pot procedure was developed to access the boralactones directly from an NHC-borane (NHC-BH3) and dimethyl acetylenedicarboxylate. | |
dc.format.extent | 8 | |
dc.format.extent | 806988 | |
dc.language.iso | eng | |
dc.relation.ispartof | Journal of the American Chemical Society | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | BDC | en |
dc.subject | R2C | en |
dc.subject.lcc | QD | en |
dc.title | 5-endo cyclizations of NHC-boraallyl radicals bearing ester substituents : characterization of derived 1,2-oxaborole radicals and boralactones | en |
dc.type | Journal article | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1021/jacs.8b09288 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2019-10-29 |
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