Decarboxylative cross-coupling reactions for P(O)–C bond formation

Hosseinian, Akram; Nasab, Fatemeh Alsadat Hosseini; Ahmadi, Sheida; Rahmani, Zahra; Vessally, Esmail

doi:10.1039/c8ra04557g

Cited by 43 publications

(13 citation statements)

References 46 publications

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“…Carboxylic acids are available at low cost in great structural diversity from both natural and synthetic sources and their application in organic synthesis has attracted much attention , . Direct utilization of carboxylic acids instead of organohalides to couple with P(O)–H compounds would greatly promote the green synthesis of organophosphorus compounds.…”

Section: Methodsmentioning

confidence: 99%

“…In 2014, Xiao disclosed a Pd/Ag co‐catalyzed decarboxylative coupling of electron‐deficient o ‐nitrobenzoic acids with H‐phosphonates (Scheme B, path 4). [12b] This reaction was conducted under microwave conditions with the use of LiNO 3 as an oxidant. Despite the high reaction rate, low yields (< 65 %) and narrow substrate scope were suffered.…”

Section: Methodsmentioning

confidence: 99%

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Palladium‐Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)–H Compounds

2020

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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 results well demonstrated the potential synthetic value of this new reaction in organic synthesis.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Palladium‐Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)–H Compounds

2020

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“…In continuation of preceding reviews on cross‐coupling reactions, we summarize here the most representative and interesting reports on the synthesis of cyclic diaryl ketones via intramolecular cross‐dehydrogenative coupling of corresponding benzaldehydes (Figure ). The synthesis of acridones is discussed first.…”

Section: Introductionmentioning

confidence: 95%

“…The transition metal‐catalyzed cross‐coupling reactions are one of the most essential and powerful tools available for synthetic chemists to create various carbon–carbon and carbon‐heteroatom bonds. In particular, cross‐dehydrogenative couplings of two different C(X)–H bonds are extremely interesting and valuable due to the minimization of waste and the costs associated with the prefunctionalization of starting materials .…”

Section: Introductionmentioning

confidence: 99%

Intramolecular cross‐dehydrogenative coupling of benzaldehyde derivatives: A novel and efficient route to benzocyclic ketones

Sheykhahmad

2019

J Chinese Chemical Soc

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Benzocyclic ketones are not only found throughout many natural products and synthetic pharmaceutically active compounds but also used as versatile building blocks in organic synthesis. In view of their importance, many researchers have been working to explore novel and efficient synthetic routes for this class of carbonyl compounds. Recently, cross-dehydrogenative coupling reactions have emerged as one of the most versatile and powerful synthetic strategies to construct various carbon-carbon and carbon-heteroatom bonds. In this regard, direct acylation of (hetero)arenes with aldehydes through C(sp 2 )-H activation opened up a new page on the synthesis of the titled compounds. In this focus-review, we discuss the most representative and important reports on the synthesis of cyclic diaryl ketones through intramolecular cross-dehydrogenative coupling reactions of corresponding benzaldehydes with emphasis on the mechanistic aspects of the reactions.

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“…The decarboxylative C−P cross‐coupling reactions between carboxylic acids and P(O)−H species have emerged as one of the most reliable and robust tools for the construction of P(O)−C bonds . In this context, in 2011, Yang et al.…”

Section: Direct Phosphorylation Of the Parent Heterocyclesmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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Decarboxylative cross-coupling reactions for P(O)–C bond formation

Abstract: Phosphorus-containing compounds are one of the most important classes of organic compounds, which have wide applications in organic chemistry, medicinal chemistry, agricultural chemistry, and materials chemistry.

Cited by 43 publications

References 46 publications

Palladium‐Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)–H Compounds

Palladium‐Catalyzed Direct Decarbonylative Phosphorylation of Benzoic Acids with P(O)–H Compounds

Intramolecular cross‐dehydrogenative coupling of benzaldehyde derivatives: A novel and efficient route to benzocyclic ketones

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

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