Reduction of Triphenylphosphine Oxide to Triphenylphosphine by Phosphonic Acid

Xiao, Jing; Wang, Jie; Zhang, Huimin; Zhang, Jianqiu; Han, Li‐Biao

doi:10.1021/acs.joc.2c02807

Cited by 11 publications

(5 citation statements)

References 51 publications

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“…Although the detailed mechanism is not clear, on the basis of these control experiments and previous reports, − we propose a reasonable reaction mechanism in Scheme . With respect to aromatic aldehyde, there are two possible pathways of the reaction.…”

supporting

confidence: 56%

Reductive Coupling of P(O)–H Compounds and Aldehydes for the General Synthesis of Phosphines and Phosphine Oxides

Wang,

Xiao,

Tang

et al. 2024

J. Org. Chem.

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A novel strategy for the selective construction of a C(sp 3 )−P(III) or −P(V) bond from >P(O)−H compounds and aldehydes is disclosed. By using the H 3 PO 3 /I 2 system, various secondary phosphine oxides could react with both aromatic and aliphatic aldehydes to afford valuable phosphines (isolated as sulfides) and phosphine oxides in good yields. This method features a wide substrate scope and simple reaction conditions and avoids the use of toxic halides and metals.

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supporting

confidence: 56%

Reductive Coupling of P(O)–H Compounds and Aldehydes for the General Synthesis of Phosphines and Phosphine Oxides

Wang,

Xiao,

Tang

et al. 2024

J. Org. Chem.

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“…Notably, the reactions proceeded smoothly under mild conditions at room temperature, making it a suitable method for practical purposes (Scheme 52). 100…”

Section: Short Review Synthesismentioning

confidence: 99%

Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

Mukherjee,

Kundu,

Das

et al. 2023

Synthesis

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The development of stereoselective synthetic routes for C-glycosides has attracted immense attention from carbohydrate chemists in the last two decades. In this review, progress made in the last decade towards the synthesis of C-glycosides using glycals as a precursor are discussed. Glycals have been extensively manipulated to generate oxocarbenium cation or glycosyl anion to form C-C bond at the anomeric position through attack with C-nucleophiles or transition metal catalyzed coupling reactions. Recent reports on carbon Ferrier, intramolecular Cope, Claisen rearrangements, various coupling reactions in the presence or absence of directing groups are deliberated herein. Contemporary applications of these reactions in the syntheses of natural products, drugs and scaffolds with bioactive potential are briefly discussed.

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“…We are currently studying new ways for transforming Ph 3 PO, the side product from the Wittig reaction etc. , into more valuable phosphorus compounds, 4 and came to know, as described above, that Ph 3 PS is a more troublesome industrial chemical waste product.…”

Section: Introductionmentioning

confidence: 99%