Catalytic Rearrangements and Allylation Reactions in Water

Cadierno, Victorio; García‐Álvarez, Joaquín; García‐Garrido, Sergio E.

doi:10.1002/9783527656790.ch7

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Reactions Involving Highly Polar Organotin Reagents or Highl...1

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Cited by 4 publications

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“…The use of water in organic , and organometallic − reactions can be considered beneficial, when a minor amount of organic solvent is required to recover the products at the end of the reaction, because it is more environmentally benign than volatile and sometimes quite toxic organic solvents. In addition, water is abundant, cheap, and can stabilize polar or ionic intermediates.…”

Section: Reactions Involving Highly Polar Organotin Reagents or Highl...mentioning

confidence: 99%

Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

et al. 2015

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Section: Reactions Involving Highly Polar Organotin Reagents or Highl...mentioning

confidence: 99%

Methodologies Limiting or Avoiding Contamination by Organotin Residues in Organic Synthesis

et al. 2015

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Exploring Green Solvents Associated to Pd/C as Heterogeneous Catalyst for Direct Arylation of Heteroaromatics with Aryl Bromides

2018

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Metal residues are certainly one of the major sources of contamination of products in metalcatalyzed direct arylation reactions. We found that the use of only 1 mol% of the heterogeneous catalyst Pd/C promotes very efficiently the direct arylations of most heteroaromatics. In the presence of this catalyst and potassium acetate as the base, the direct arylation of thiophenes, furans, pyrroles, thiazoles, imidazoles or isoxazoles, using aryl bromides as coupling partners, proceeds highly regioselectively and in moderate to very high yields. With several heteroarenes both electron-deficient and electron-rich aryl bromides were tolerated; moreover, with the most reactive heteroarenes, the Pd/C catalyst tolerated green solvents such as diethyl carbonate, 3-methylbutan-1-ol and pentan-1-ol, affording a synthetic scheme with low environmental impact.

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