Hydrogenolysis

Smith, Gerard V.

doi:10.1016/b978-012651645-6/50004-4

Cited by 2 publications

(2 citation statements)

References 506 publications

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“…For compound 26 we propose involvement of the 3-OH group, however, reaction of the 5-OH group providing a constitutional isomer of the drawn product cannot be excluded. The generation of formaldehyde from methanol in the presence of palladium catalysts is a process well known in the literature [27] and has also been observed in earlier studies of our group. [20,27d] A similar result was obtained with the divalent compound 14 which provided 27 and 28 as products (ratio ca.…”

Section: Resultssupporting

confidence: 72%

Multivalent Aminoseptanose Mimetics by Copper‐Catalyzed (3+2) Cycloadditions of Azidomethyl‐Substituted Bicyclic 1,2‐Oxazines

Bouché,

Zimmer,

Reissig

2024

Eur J Org Chem

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Starting from readily available enantiopure azidomethyl‐substituted bicyclic 1,2‐oxazine derivatives and mono‐, di‐ or trialkynes, their copper‐catalyzed (3+2) cycloadditions furnished a series of 1,2,3‐triazolyl‐linked compounds in good yields. These click reactions proceeded smoothly at room temperature when copper iodide as catalyst was used in the presence of triethylamine and tris[(1‐benzyl‐1H‐1,2,3‐triazol‐4‐yl)methyl]amine as ligand. Generally, the unprotected bicyclic 1,2‐oxazine derivatives seemed to show slightly higher reactivity and provided better yields compared with their silyl‐protected counterparts. Exhaustive hydrogenolysis with cleavage of the 1,2‐oxazine N‐O bonds in the presence of palladium on charcoal as promotor is feasible but was found to be capricious. Reasonable results were obtained when acetic acid employed as cosolvent. By applying these conditions, several of the bicyclic 1,2‐oxazine derivatives were successfully converted into the expected mono‐ or divalent aminooxepine derivatives which can be regarded as aminoseptanose mimetics.

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Section: Resultssupporting

confidence: 72%

Multivalent Aminoseptanose Mimetics by Copper‐Catalyzed (3+2) Cycloadditions of Azidomethyl‐Substituted Bicyclic 1,2‐Oxazines

Bouché,

Zimmer,

Reissig

2024

Eur J Org Chem

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“…On the other hand, the use of heterogeneous catalysts has been widely studied because they are easy to remove from the reaction media by simple filtration after completion of the reaction and in general, they are reusable without appreciable loss of their catalytic activity [37,38].…”

Section: Introductionmentioning

confidence: 99%

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

et al. 2015

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4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H 14 P 5 NaW 30 O 110 ) (PA) as heterogeneous catalyst under solvent-free reaction conditions, at 130 °C, in a short reaction time (2 h). Under these conditions, very good yields (11 examples: 61 %-90 %), free of secondary products, were obtained. The catalyst is recyclable, nontoxic, neither air nor moisture sensitive, and easy to handle. The described methodology is a clean and useful alternative to synthesize oxygenated heterocycles based on a coumarin skeleton.

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Hydrogenolysis

Cited by 2 publications

References 506 publications

Multivalent Aminoseptanose Mimetics by Copper‐Catalyzed (3+2) Cycloadditions of Azidomethyl‐Substituted Bicyclic 1,2‐Oxazines

Multivalent Aminoseptanose Mimetics by Copper‐Catalyzed (3+2) Cycloadditions of Azidomethyl‐Substituted Bicyclic 1,2‐Oxazines

Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions

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