Reduction of tertiary phosphine oxides to phosphine-boranes using Ti(Oi-Pr)4/BH3-THF

Sowa, Sylwia; Pietrusiewicz, K. Michał

doi:10.1016/j.tet.2021.132057

Cited by 3 publications

(1 citation statement)

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“…As a comparison, the method described herein exhibits apparent advantages over the reported method. Further, starting from the phosphine oxide 7 , other types of derivatives such as phosphine sulfide 9 , phosphine 10 , and the aromatized phosphine oxide 11 and the reduced phosphine 12 were also synthesized smoothly in high yields.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr₃ and P(OMe)₃ as the P^(III) Source

Han

2023

J. Org. Chem.

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An efficient method for the synthesis of 1-hydroxy-2,5-dihydrophosphole 1-oxides, a type of five-membered Pcontaining heterocyclic compound, is presented. The reaction was carried out through a [4C+1P] cyclization of 1,3-dienes with a combination of PBr 3 and P(OMe) 3 as the P (III) source. To compare with the reported methods, the protocol reported herein not only is much milder and more rapid but also displays a broad substrate scope and affords the products in high yields (50−94%). In addition, the reaction could be reliably scaled up at the gram-scale level and was demonstrated to be a versatile platform for flexible derivatization. Consequently, this method provides a general and reliable way for the synthesis of five-membered phosphole derivatives.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr₃ and P(OMe)₃ as the P^(III) Source

Han

2023

J. Org. Chem.

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Palladium-Catalyzed Coupling of Aryl Chlorides with Secondary Phosphines to Construct Unsymmetrical Tertiary Phosphines

Xiao,

Yang,

et al. 2024

Org. Lett.

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The functionalization of the C−Cl bond in unactivated aryl chlorides under mild conditions presents a significant challenge. We disclose a general protocol for constructing both partially and entirely unsymmetrical tertiary phosphines through the Pd/keYPhos-catalyzed coupling of aryl chlorides with secondary phosphines under mild conditions. The reaction exhibits excellent functional group tolerance and broad substrate scopes. Furthermore, the rapid synthesis of ligands and luminescent compound sTPPs, alongside gram-scale systhesis, demonstrates the practical applicability of this method.

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Phosphine chalcogenides

Keglevich

2024

Organophosphorus Chemistry

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This chapter gives an account of newer developments in the synthesis and reactivity of phosphine chalcogenides, mainly oxides and sulfides, during 2020. A series of new synthetic methods for phosphine oxides is discussed, followed by preparations utilizing simple P-reagents such as P(iii)- and P(v)-chlorides, and >P(O)H species. Their additions to unsaturated substrates and P–C coupling reactions, involving interesting variations, represent a hot topic. The modification of P-chalcogenides including deoxygenations are also shown. Optically active phosphine oxides and their complexes also form a usual part of this chapter.

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Reduction of tertiary phosphine oxides to phosphine-boranes using Ti(Oi-Pr)4/BH3-THF

Cited by 3 publications

References 65 publications

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr₃ and P(OMe)₃ as the P^(III) Source

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr₃ and P(OMe)₃ as the P^(III) Source

Palladium-Catalyzed Coupling of Aryl Chlorides with Secondary Phosphines to Construct Unsymmetrical Tertiary Phosphines

Phosphine chalcogenides

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Reduction of tertiary phosphine oxides to phosphine-boranes using Ti(Oi-Pr)4/BH3-THF

Cited by 3 publications

References 65 publications

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr3 and P(OMe)3 as the P(III) Source

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr3 and P(OMe)3 as the P(III) Source

Palladium-Catalyzed Coupling of Aryl Chlorides with Secondary Phosphines to Construct Unsymmetrical Tertiary Phosphines

Phosphine chalcogenides

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Product

Resources

About

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr₃ and P(OMe)₃ as the P^(III) Source

Synthesis of Five-Membered Cyclic Phosphinic Acids via the [4C+1P] Cyclization of 1,3-Dienes with a Combination of PBr₃ and P(OMe)₃ as the P^(III) Source