Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C–H bonds: synthesis of α-aminophosphonates under aerobic conditions

Alagiri, Kaliyamoorthy; Devadig, Pradeep; Prabhu, Kandikere Ramaiah

doi:10.1016/j.tetlet.2012.01.031

Cited by 49 publications

(12 citation statements)

References 45 publications

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“…Similar reactions have been also studied by using an Au complex, MoO 3 , zero‐valent nanoporous gold (AuNPore), a binuclear copper complex [{Cu(Sal) 2 (NCMe)} 2 ] (Sal=salicylate), FeCl 2 , Co(OAc) 2 , CoNiFe hydrotalcite, and NaSbCl 6 (α‐NaphNO 2 ) as transition metal catalysts (Table ). A reaction mechanism that involved oxidation of a tertiary amine to a highly reactive cationic iminium species under metal catalysis and an O 2 atmosphere with subsequent nucleophilic addition of such a species by P(O)−H compounds was considered.…”

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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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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“…In addition to the reactions described above, this sp 3 C-H/P(O)-H dehydrogenative coupling could also be achieved by using MoO 3 , 40 iodine, 41 SO 2 Cl 2 , 42 triarylaminium salts, 43 DDQ 44 and AIBN. 45 However, it should be pointed out that, currently, the sp 3 C-H compound was restricted to tertiary amines and an excess amount of P(O)H compounds often were used in these sp 3 C-H/P(O)-H dehydrogenative couplings.…”

Section: Constructing Sp 2 C-p Bondsmentioning

confidence: 99%

Dehydrogenative coupling involving P(O)–H bonds: a powerful way for the preparation of phosphoryl compounds

2016

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Because of the unique properties and wide applications, continuing efforts have been devoted to developing simpler and cleaner methods for the synthesis of organophosphorus compounds. Recently, transition metal-catalysed dehydrogenative coupling has been emerging as one of the powerful methodologies for constructing chemical bonds. Herein, we highlight the recent progress in the preparation of organophosphorus compounds via transition metal-catalysed dehydrogenative couplings of P(O)H compounds with Z-H compounds.

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“…[2] Therefore, the combination of structures of THIQs and α‐aminophosphonates has attracted significant attention from organic synthesis. However, not many reports were published about the synthesis of α‐aminophosphonates THIQs . Among these results, most cases need N‐protected THIQs as starting materials and oxidants…”

Section: Introductionmentioning

confidence: 99%

“…However, not many reports were published about the synthesis of a-aminophosphonates THIQs. [3][4][5][6][7][8][9][10][11] Among these results, most cases need N-protected THIQs as starting materials [12] and oxidants. [13] Zhao's group firstly reported an efficient and facile silvercatalyzed, aldehyde-induced a-CÀH Functionalization of THIQs with concurrent CÀP bond formation/N-alkylatioin.…”

Section: Introductionmentioning

confidence: 99%

One Step Carbon‐Phosphor Bond Formation and N‐Alkylation of Tetrahydroisoquinolines under Silver Catalysis

Fan

Zhang

et al. 2017

ChemistrySelect

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Heterocycles with tetrahydroisoquinolines moiety are important biologically, and α‐aminophosphonates derivatives have unusual features in agrochemicals and medicines. In this paper, we combined these two parts to afford α‐aminophosphonates tetrahydroisoquinolines. A highly facile, one step direct carbon‐phosphor bond formation and N‐alkylation of tetrahydroisoquinolines was developed. It is a three‐component reaction of Nitrogen‐unprotected tetrahydroisoquinolines, aldehydes and trialkyl phosphites, which provides C1‐phosphonylated and N‐alkylation of THIQs (Tetrahydroisoquinolines) with moderate to high yields. The mild reaction conditions were investigated to give a broad range of substrates. Under the optimized reaction condition at reaction temperature 120 oC, after heating 8 h the desired final product was given in 90% yield, which is a satisfied reaction result. The different substituted benzaldehydes and THIQs were investigated in detail and proved to be broad. The proposed mechanism was also showed.

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Molybdenum trioxide catalyzed oxidative cross-dehydrogenative coupling of benzylic sp3 C–H bonds: synthesis of α-aminophosphonates under aerobic conditions

Cited by 49 publications

References 45 publications

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

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

Dehydrogenative coupling involving P(O)–H bonds: a powerful way for the preparation of phosphoryl compounds

One Step Carbon‐Phosphor Bond Formation and N‐Alkylation of Tetrahydroisoquinolines under Silver Catalysis

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