Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes

Zhan, Jun-Long; Wang, Bing-Jie; Wang, Chen-Xi; Zhao, Xin-Ming; Zhou, Sai-Nan; Dou, Zao-Zao; Yang, Xin-Xin; Zhu, Lin; Ren, Wei

doi:10.1039/d3ob00607g

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00607g

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Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes

Jun-Long Zhan,

Bing-Jie Wang,

Chen-Xi Wang

et al.

Abstract: A copper-catalyzed unprotected hydroxylamine mediated phosphorylation of alkenes furnished structurally important (E)-alkenylphosphine oxides under mild reaction conditions with good functional group tolerance and excellent regioselectivity.

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Cited by 3 publications

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Formal Olefinic C−H Phosphinylation via Alkenyl Sulfonium Salts

Ma,

Lin,

et al. 2024

Adv Synth Catal

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Formal olefinic C−P cross‐coupling between alkenyl sulfonium salts and secondary phosphine oxides and H‐phosphinates has been developed. A base enables construction of alkenyl C−P bonds as well as aliphatic C−P bonds at ambient temperature under an air atmosphere. This protocol provides an alternative access to multisubstituted alkenyl phosphine oxides and phosphinates in 40‐99% yields from functionalized alkenes through an interrupted Pummerer activation/base‐promoted olefinic C−S bond phosphinylation sequence. The gram‐scale preparation and feasible derivatization have demonstrated the applicability of the resultant alkenylphosphine oxides.

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Formal Olefinic C−H Phosphinylation via Alkenyl Sulfonium Salts

Ma,

Lin,

et al. 2024

Adv Synth Catal

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N‐Protection Dependent Phosphorylation of Dehydroamino Acids to Build Unusual Phosphono‐Peptides

Kothuri,

Bhumannagari,

Battula

et al. 2024

Chemistry An Asian Journal

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An efficient Mn(III)‐promoted phosphorylation of dehydroalanine (Dha) has been developed to give unusual α‐amino acids bearing phosphonates/phosphine oxides and β‐vinyl phosphonates/phosphinates depending on N‐protection of amino acid. N,N‐diprotected dehydroalanine reacted with H‐phosphonates and H‐phosphine oxides to give structurally diverse phosphorylated α‐amino acids through conjugate addition of phosphorous radical generated by Mn(OAc)3.2H2O. Whereas, a highly Z‐selective phosphorylation was observed in the case of mono N‐Boc protected dehydroalanine via cross dehydrogenative coupling to give (Z)‐ β ‐vinyl phosphono amino acid. The method is successfully applied to short peptides to derive unusual phosphono‐peptides under mild conditions.

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Transition metal-free [3 + 3] annulation of cyclopropanols with β-enamine esters to assemble nicotinate derivatives

Zhan,

Zhu,

Bai

et al. 2023

Org. Biomol. Chem.

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Copper-catalyzed 4-HO-TEMPOH mediated phosphorylation of alkenes

Abstract: A copper-catalyzed unprotected hydroxylamine mediated phosphorylation of alkenes furnished structurally important (E)-alkenylphosphine oxides under mild reaction conditions with good functional group tolerance and excellent regioselectivity.

Cited by 3 publications

References 59 publications

Formal Olefinic C−H Phosphinylation via Alkenyl Sulfonium Salts

Formal Olefinic C−H Phosphinylation via Alkenyl Sulfonium Salts

N‐Protection Dependent Phosphorylation of Dehydroamino Acids to Build Unusual Phosphono‐Peptides

Transition metal-free [3 + 3] annulation of cyclopropanols with β-enamine esters to assemble nicotinate derivatives

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