A new double functionalization reaction of alkenes through AgNO-mediated phosphinoyl radical addition followed by Cu(II)-catalyzed amination is introduced. This one-pot, three-component reaction is performed under mild conditions to afford α,β-aminophosphinoylation products.
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http://dx.doi.org/10.1021/acs.orglett.7b02183 | DOI Listing |
Org Lett
June 2024
Division of Molecular Catalysis and Synthesis, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. China.
The radical 1,4-functionalizations of 1,3-enynes have emerged as a powerful strategy for the synthesis of multisubstituted allenes. However, the phosphorus-centered radical-initiated transformations remain largely elusive. Herein, visible-light photoredox catalytic regioselective radical hydrophosphinylation of 1,3-enynes with diaryl phosphine oxides as phosphinoyl radical precursors has been realized.
View Article and Find Full Text PDFOrg Lett
June 2021
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry and Chemical Engineering, Soochow University, Suzhou, Jiangsu 215123, China.
A copper-catalyzed difunctional cyano-, thiocyano-, and chlorophosphorylation reaction of alkynes with P(O)-H compounds and coupling partners (TBACN, TMSNCS, TMSCl) is described. The reaction introduces versatile groups (-P(O)R and -CN, -SCN, or -Cl) to form tri- and tetrasubstituted alkenyl phosphine oxides/phosphonates regio- and stereoselectively.
View Article and Find Full Text PDFJ Org Chem
February 2018
Department of Chemistry, University of Massachusetts Boston, Boston, Massachusetts 02125, United States.
1,2-Bifuctional thiocyanodiphenylphosphinoylation of alkenes is established through the phosphinoyl radical addition followed by Cu-catalyzed thiocyanation. This one-pot reaction is applicable to a range of aromatic, aliphatic, and cyclic alkenes to afford thiocyanodiphenylphosphinoylated compounds in satisfactory yields.
View Article and Find Full Text PDFOrg Lett
October 2017
Department of Chemistry, University of Massachusetts, Boston, Massachusetts 02125, United States.
A double-functionalization reaction of alkenes through Mn(OAc)-mediated phosphinoyl radical addition followed by CuCN-catalyzed cyanation is introduced. This one-pot reaction is performed under mild conditions to afford vicinal cyanophosphinoylation products.
View Article and Find Full Text PDFOrg Lett
September 2017
Department of Chemistry, University of Massachusetts Boston, Massachusetts 02125, United States.
A new double functionalization reaction of alkenes through AgNO-mediated phosphinoyl radical addition followed by Cu(II)-catalyzed amination is introduced. This one-pot, three-component reaction is performed under mild conditions to afford α,β-aminophosphinoylation products.
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