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Literature DB >> 10891219

Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols.

Abstract

[reaction: see text] The cross-coupling of aryl boronic acids and alkanethiols mediated by copper(II) acetate and pyridine in anhydrous dimethylformamide affords aryl alkyl sulfides in good yield with a wide variety of substituted aryl boronic acids. The method is applicable to the synthesis of aryl sulfides of cysteine.

Entities: Chemical

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Year: 2000 PMID： 10891219 DOI： 10.1021/ol005832g

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

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Cited

11 in total

Review 1. Aerobic copper-catalyzed organic reactions.

Authors: Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal: Chem Rev Date: 2013-06-20 Impact factor: 60.622

2. Copper Mediated Coupling of 2-(Piperazine)-pyrimidine Iodides with Aryl Thiols using Cu(I)Thiophene-2-carboxylate.

Authors: Liza Shrestha; Hardik J Patel; Yanlong Kang; Sahil Sharma; Gabriela Chiosis; Tony Taldone
Journal: Tetrahedron Lett Date: 2017-10-23 Impact factor: 2.415

3. Synthesis of Copper(I) Thiolate Complexes in the Thioetherification of Aryl Halides.

Authors: Chaohuang Chen; Zhiqiang Weng; John F Hartwig
Journal: Organometallics Date: 2012-10-04 Impact factor: 3.876

4. Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization.

Authors: Alexander B Draganov; Ke Wang; Jalisa Holmes; Krishna Damera; Danzhu Wang; Chaofeng Dai; Binghe Wang
Journal: Chem Commun (Camb) Date: 2015-10-21 Impact factor: 6.222

Copper-mediated cross-coupling of aryl boronic acids and alkyl thiols.

Review 1. Aerobic copper-catalyzed organic reactions.

2. Copper Mediated Coupling of 2-(Piperazine)-pyrimidine Iodides with Aryl Thiols using Cu(I)Thiophene-2-carboxylate.

3. Synthesis of Copper(I) Thiolate Complexes in the Thioetherification of Aryl Halides.

4. Click with a boronic acid handle: a neighboring group-assisted click reaction that allows ready secondary functionalization.

5. N-substituted imines by the copper-catalyzed N-imination of boronic acids and organostannanes with O-acyl ketoximes.

6. A new paradigm for carbon-carbon bond formation: aerobic, copper-templated cross-coupling.

7. Diethyl 5,5'-thio-bis[2-amino-4-(4-fluoro-phen-yl)-1-phenyl-1H-pyrrole-3-carboxyl-ate].

8. Environmentally benign approach towards C-S cross-coupling reaction by organo-copper(II) complex.

9. Copper(II)-mediated O-arylation of protected serines and threonines.

10. Microwave Application and Anhydrous Cu(OAc)₂ Mediated O-Arylation of Aliphatic Amino Alcohols.