Herein, we describe an efficient method for the synthesis of alkenylphosphine oxides a TfO promoted addition-elimination process. Various diarylphosphine oxides and alkylarylphosphine oxides react with ketones smoothly and produce alkenylphosphine oxides in moderate to excellent yields with abundant functional group compatibility. In addition, several transformations and applications of the product also demonstrate the potential value of the methodology.
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http://dx.doi.org/10.1039/d4ob00318g | DOI Listing |
Org Biomol Chem
December 2024
Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361001, Fujian, People's Republic of China.
A novel and transition-metal-free hydrophosphinylation of allenes with secondary phosphine oxides was developed. In the presence of the cheap and commercially available cesium carbonate, various hydrophosphinylation products were synthesized with exclusive regio- and stereoselectivity under mild conditions. This methodology provides simple and efficient access to ()-alkenylphosphine oxides in moderate to excellent yields with a relatively broad substrate scope.
View Article and Find Full Text PDFOrg Biomol Chem
May 2024
Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, P. R. China.
Herein, we describe an efficient method for the synthesis of alkenylphosphine oxides a TfO promoted addition-elimination process. Various diarylphosphine oxides and alkylarylphosphine oxides react with ketones smoothly and produce alkenylphosphine oxides in moderate to excellent yields with abundant functional group compatibility. In addition, several transformations and applications of the product also demonstrate the potential value of the methodology.
View Article and Find Full Text PDFOrg Biomol Chem
June 2023
Henan Scientific Research Platform Service Center, Zhengzhou, Henan 450000, P. R. China.
An efficient, practical and regioselective synthesis of ()-alkenylphosphine oxides has been developed starting from alkenes under copper catalysis and 4-HO-TEMPOH oxidation. Preliminary mechanistic studies clearly reveal that a phosphinoyl radical is involved in this process. Moreover, this method features mild reaction conditions, good functional group tolerance, and excellent regioselectivity and also promises to be efficient for the late-stage functionalization of drug molecular skeletons.
View Article and Find Full Text PDFJ Org Chem
December 2021
School of Chemical Sciences, National Institute of Science Education and Research (NISER), HBNI, Bhubaneswar, 752050, India.
Herein, a catalytic cross-coupling of methyldiphenylphosphine oxide with arylmethyl alcohols leading to the alkenylphosphine oxides is reported. A manganese pincer catalyst catalyzes the reactions, which provides exclusive formation of -alkenylphosphine oxides. Mechanistic studies indicate that reactions proceed via aldehyde intermediacy and the catalyst promotes the C═C bond formation.
View Article and Find Full Text PDFJ Org Chem
August 2021
School of Public Health, Xinxiang Medical University, Xinxiang 453003, China.
A Pd-catalyzed difluoroalkylation/cyclization/phosphinoylation of 2-vinyloxy arylalkynes with ethyl difluoroiodoacetate and diarylphosphine oxides has been successfully developed. This reaction allows the formation of C-CF, C-C, and C-P(O) bonds in one step, providing a straightforward route to difluoroalkyl-containing tetrasubstituted alkenylphosphine oxides with complete stereoselectivities under mild conditions.
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