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Literature DB >> 19402681

Amination of allylic alcohols in water at room temperature.

Abstract

The "trick" to carrying out regiocontrolled aminations of allylic alcohols in water as the only medium is use of a nanomicelle's interior as the organic reaction solvent. When HCO(2)Me is present, along with the proper base and source of catalytic Pd, allylic amines are cleanly formed at room temperature.

Entities: Chemical Disease Gene

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Year: 2009 PMID： 19402681 PMCID： PMC3359138 DOI： 10.1021/ol900235s

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

11 in total

1. Nickel-catalyzed cross-coupling of aryl grignard reagents with aromatic alkyl ethers: an efficient synthesis of unsymmetrical biaryls.

Authors: John W Dankwardt
Journal: Angew Chem Int Ed Engl Date: 2004-04-26 Impact factor: 15.336

2. Reactions in micellar systems.

Authors: Torsten Dwars; Eckhard Paetzold; Günther Oehme
Journal: Angew Chem Int Ed Engl Date: 2005-11-11 Impact factor: 15.336

3. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update.

Authors: Chao-Jun Li
Journal: Chem Rev Date: 2005-08 Impact factor: 60.622

Review 4. Reactions of C-H bonds in water.

Authors: Clara I Herrerías; Xiaoquan Yao; Zhiping Li; Chao-Jun Li
Journal: Chem Rev Date: 2007-04-17 Impact factor: 60.622

6. Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies.

Authors: Takashi Nishikata; Alexander R Abela; Shenlin Huang; Bruce H Lipshutz
Journal: Beilstein J Org Chem Date: 2016-05-20 Impact factor: 2.883

6 in total

Amination of allylic alcohols in water at room temperature.

1. Nickel-catalyzed cross-coupling of aryl grignard reagents with aromatic alkyl ethers: an efficient synthesis of unsymmetrical biaryls.

2. Reactions in micellar systems.

3. Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update.

Review 4. Reactions of C-H bonds in water.

5. Micellar catalysis of Suzuki-Miyaura cross-couplings with heteroaromatics in water.

6. Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

7. Aminations of Aryl Bromides in Water at Room Temperature.

8. Facile and selective deallylation of allyl ethers using diphosphinidenecyclobutene-coordinated palladium catalysts.

9. Metal-catalyzed enantioselective allylation in asymmetric synthesis.

10. Nickel-catalyzed cross-coupling of aryl methyl ethers with aryl boronic esters.

1. "Designer"-Surfactant-Enabled Cross-Couplings in Water at Room Temperature.

2. TPGS-750-M: a second-generation amphiphile for metal-catalyzed cross-couplings in water at room temperature.

3. Pd-catalyzed synthesis of allylic silanes from allylic ethers.

4. Amination of allylic alcohols in water at room temperature.

5. Aminations of allylic phenyl ethers via micellar catalysis at room temperature in water.

6. Cationic Pd(II)-catalyzed C-H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies.