2020
DOI: 10.1002/ejoc.201901865
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Abstract: A direct decarbonylative phosphorylation of benzoic acids catalyzed by palladium was disclosed. Under the reaction conditions, a wide range of benzoic acids coupled readily with all the three kinds of P(O)–H compounds, i.e. secondary phosphine oxides, H‐phosphinates and H‐phosphonates, producing the corresponding organophosphorus compounds in good to high yields. This reaction could be conducted at a gram scale and applied in the late‐stage phosphorylative modification of carboxylic acids drug molecules. These… Show more

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Cited by 31 publications
(14 citation statements)
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References 114 publications
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“…It should be noted that a low yield was obtained when Boc 2 O was used as the activating reagent for carboxylic acids in this reaction, which would be due to the thermal decomposition of Boc 2 O at the reaction temperature of 160 °C used. Our group has achieved this reaction using Boc 2 O at a lower temperature (115 °C) 30 with wide substrate scope for the benzoic acids. Worth noting is that the three different hydrogen phosphoryl compounds, i.e.…”
Section: Short Review Synthesismentioning
confidence: 99%
“…It should be noted that a low yield was obtained when Boc 2 O was used as the activating reagent for carboxylic acids in this reaction, which would be due to the thermal decomposition of Boc 2 O at the reaction temperature of 160 °C used. Our group has achieved this reaction using Boc 2 O at a lower temperature (115 °C) 30 with wide substrate scope for the benzoic acids. Worth noting is that the three different hydrogen phosphoryl compounds, i.e.…”
Section: Short Review Synthesismentioning
confidence: 99%
“…It is possible to subject the enantiomerically enriched 4carboxylic acid 13a to a decarboxylative phosphorylation to give the phosphine oxide 14 in 8-20% (along with 50% unreacted starting material with no erosion of enantiopurity (Scheme 3). [35][36][37] So far, we have been unable to react the pseudoortho-diacid under the same conditions. Although the preliminary results are low yielding, they demonstrate that it is possible to isolate enantiomerically enriched phosphine oxide in just four steps.…”
Section: Table 1 Scope Of Oxazoline Coupling (Only Single Diastereois...mentioning
confidence: 99%
“…To date, a number of variations of the P–C couplings were developed comprising in situ formed catalysts from suitable precursors, such as Pd(OAc) 2 and PdCl 2 , and different added mono- or bidentate P-ligands. The protocol was extended to H -phosphinates, as well as secondary phosphine oxides applying a wide range of arenes [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. Later on, Ni- and Cu complexes were also used as catalysts [ 10 , 11 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 ].…”
Section: Introductionmentioning
confidence: 99%