Synthesis and olefination of carbonyl compounds using solid-supported reagents

Hansen, Anne-Lene L.; Murray, Anthony; Tanner, David

doi:10.1039/b612944g

Cited by 5 publications

(4 citation statements)

References 42 publications

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“…The reaction of 1,10-phenanthroline (9.0 mg, 0.05 mmol), 2,2'-bipyridine (8.0 mg, 0.05 mmol), CuCl (9.8 mg, 0.10 mmol), K 2 CO 3 (34.2 mg, 0.25 mmol), dry toluene (2.5 mL), DBAD (22.7 mg, 0.10 mmol), and 1g (87.2 mg, 0.5 mmol)/dry toluene (2.5 mL) afforded 2g [28] . The reaction of 1,10-phenanthroline (4.4 mg, 0.025 mmol), 2,2'-bipyridine (3.8 mg, 0.025 mmol), CuCl (5.0 mg, 0.05 mmol), K 2 CO 3 (34.2 mg, 0.25 mmol), dry toluene (2.5 mL), DBAD (11.7 mg, 0.05 mmol), and 1g (87.0 mg, 0.5 mmol)/dry toluene (2.5 mL) afforded 2g [28] (71.2 mg, 83%) (eluent: petroleum ether∶ethyl acetate ＝30∶1): Liquid.…”

Section: -Phenylhex-2-yn-1-one (2g)mentioning

confidence: 99%

“…The reaction of 1,10-phenanthroline (4.4 mg, 0.025 mmol), 2,2'-bipyridine (3.8 mg, 0.025 mmol), CuCl (5.0 mg, 0.05 mmol), K 2 CO 3 (34.2 mg, 0.25 mmol), dry toluene (2.5 mL), DBAD (11.7 mg, 0.05 mmol), and 1g (87.0 mg, 0.5 mmol)/dry toluene (2.5 mL) afforded 2g [28] (71.2 mg, 83%) (eluent: petroleum ether∶ethyl acetate ＝30∶1): Liquid.…”

Section: -Phenylhex-2-yn-1-one (2g)mentioning

confidence: 99%

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CuCl‐Catalyzed Aerobic Oxidation of Allylic and Propargylic Alcohols to Aldehydes or Ketones with 1:1 Combination of Phenanthroline and Bipyridine as the Ligands

Liu

2012

Chin. J. Chem.

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We developed a modified protocol for the oxidation of 2,3-allenyl alcohols using CuCl with 1∶1 combination of phenanthroline and bipyridine as the catalyst. To further investigate the applicability of this system, other types of alcohols such as allylic and propargylic alcohols have been tested: we found that both allylic and propargylic alcohols may be oxidized to the corresponding aldehydes or ketones using molecular oxygen in air as the oxidant with moderate to excellent yields.

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Section: -Phenylhex-2-yn-1-one (2g)mentioning

confidence: 99%

Section: -Phenylhex-2-yn-1-one (2g)mentioning

confidence: 99%

CuCl‐Catalyzed Aerobic Oxidation of Allylic and Propargylic Alcohols to Aldehydes or Ketones with 1:1 Combination of Phenanthroline and Bipyridine as the Ligands

Liu

2012

Chin. J. Chem.

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“…Recently, the Tanner research group 64 reported the development and applications of three new solid-supported reagents for the synthesis of carbonyl compounds and olefins.…”

Section: Scheme 37 a Polymer-assisted Sonogashira Reactionmentioning

confidence: 99%

Solid-Supported Reagents and Catch-and-Release Techniques in Organic Synthesis

Solinas¹,

Taddei

2007

Synthesis

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The use of polymer-supported reagents, catalysts and scavengers (and their appropriate combinations) represents a powerful approach for the synthesis of organic compounds, using both traditional and parallel solution-phase methodologies, and it has been of great interest in recent years, especially in the field of pharmaceutical research. Polymer-supported synthesis circumvents the need to bind the substrate to a solid support, and thereby allows for the reactions to be monitored with familiar analytical techniques. The purpose of this publication is to review the recent synthetic transformations (from 2001) carried out with solid-supported reagents, including the catch-and-release techniques, which represent a hybrid approach in between scavenging and solid-phase synthesis.

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“…Reduction of chiral O,N-disubstituted hydroxylamines offers easy access to optically active primary amines and polyfunctional amines. The acylation of O,N-dimethylhydroxylamine affords Weinreb amides,[595][596][597][598][599] which serve as carbonyl equivalents and are extensively used in the preparation of ketones, aldehydes, and 1,2-diols. O,N-Disubstituted hydroxylamines may display bioactivity in their own right as bioisosteres of the corresponding amines or contribute to bioactivity, generally to enzyme inhibition, as an essential structural motif.…”

mentioning

confidence: 99%