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Literature DB >> 19938812

Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides.

Andrew J Ross¹, Hannah L Lang, Richard F W Jackson.

Abstract

A combination of Pd(2)(dba)(3) and SPhos (1:2 molar ratio) is an excellent precatalyst for the Negishi cross-coupling of the serine-derived organozinc reagent 2 with aryl halides, including previously difficult ortho-substituted examples. In the case of meta- and para-substituted aryl halides, Pd-loadings of 0.5 mol % give satisfactory results. Use of 2-iodoaniline as substrate gives the lactam 12 in good yield.

Entities: Chemical

Year: 2010 PMID： 19938812 DOI： 10.1021/jo902238n

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

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Cited

18 in total

1. Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: formal synthesis of (-)-haouamine A.

Authors: Erik Fenster; Charlie Fehl; Jeffrey Aubé
Journal: Org Lett Date: 2011-04-25 Impact factor: 6.005

2. Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters.

Authors: Amira H Dardir; Nilay Hazari; Scott J Miller; Christopher R Shugrue
Journal: Org Lett Date: 2019-07-10 Impact factor: 6.005

3. Malaria Box-Inspired Discovery of N-Aminoalkyl-β-carboline-3-carboxamides, a Novel Orally Active Class of Antimalarials.

Authors: Jopaul Mathew; Sha Ding; Kevin A Kunz; Emily E Stacy; Joshua H Butler; Reagan S Haney; Emilio F Merino; Grant J Butschek; Zaira Rizopoulos; Maxim Totrov; Maria B Cassera; Paul R Carlier
Journal: ACS Med Chem Lett Date: 2022-02-23 Impact factor: 4.345

Much improved conditions for the Negishi cross-coupling of iodoalanine derived zinc reagents with aryl halides.

1. Use of a tandem Prins/Friedel-Crafts reaction in the construction of the indeno-tetrahydropyridine core of the haouamine alkaloids: formal synthesis of (-)-haouamine A.

2. Palladium-Catalyzed Suzuki-Miyaura Reactions of Aspartic Acid Derived Phenyl Esters.

3. Malaria Box-Inspired Discovery of N-Aminoalkyl-β-carboline-3-carboxamides, a Novel Orally Active Class of Antimalarials.

4. Fueling the Pipeline via Innovations in Organic Synthesis.

5. Synthesis of Enantiopure Unnatural Amino Acids by Metallaphotoredox Catalysis.

6. Umpolung Ala^B Reagents for the Synthesis of Non-Proteogenic Amino Acids, Peptides and Proteins.

7. Facile conversion of chromane-6-triflate to chromane-6-alanines under Palladium conditions.

8. Synthesis and evaluation of phenylalanine-derived trifluoromethyl ketones for peptide-based oxidation catalysis.

9. Rapid Synthesis of Boc-2',6'-dimethyl-l-tyrosine and Derivatives and Incorporation into Opioid Peptidomimetics.

10. Negishi Cross-Coupling Provides Alkylated Tryptophans and Tryptophan Regioisomers.