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Literature DB >> 28345090

Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

Sébastien Laulhé¹, J Miles Blackburn, Jennifer L Roizen.

Abstract

A novel Suzuki-Miyaura protocol is described that enables the exhaustive alkylation of polychlorinated pyridines. This method facilitates a formal synthesis of normuscopyridine and the rapid assembly of a dumbbell shaped portion of a [2]rotaxane.

Entities: Chemical Disease Gene

Year: 2017 PMID： 28345090 PMCID： PMC5491353 DOI： 10.1039/c7cc00997f

Source DB: PubMed Journal: Chem Commun (Camb) ISSN： 1359-7345 Impact factor: 6.222

38 in total

1. Chemoselective sp2-sp3 cross-couplings: iron-catalyzed alkyl transfer to dihaloaromatics.

Authors: Sushant Malhotra; Pamela S Seng; Stefan G Koenig; Alan J Deese; Kevin A Ford
Journal: Org Lett Date: 2013-07-05 Impact factor: 6.005

2. Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors: Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal: J Am Chem Soc Date: 2002-06-05 Impact factor: 15.419

3. Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.

Authors: James R Colombe; Sebastian Bernhardt; Christos Stathakis; Stephen L Buchwald; Paul Knochel
Journal: Org Lett Date: 2013-10-24 Impact factor: 6.005

4. Unprecedented negishi coupling at C-br in the presence of a stannyl group as a convenient approach to pyridinylstannanes and their application in liquid crystal synthesis.

Authors: Yulia A Getmanenko; Robert J Twieg
Journal: J Org Chem Date: 2008-01-08 Impact factor: 4.354

5. Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts.

Authors: Fu-She Han
Journal: Chem Soc Rev Date: 2013-06-21 Impact factor: 54.564

6. Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen.

Authors: Qian Li; Carl W Liskey; John F Hartwig
Journal: J Am Chem Soc Date: 2014-06-05 Impact factor: 15.419

Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

1. Chemoselective sp2-sp3 cross-couplings: iron-catalyzed alkyl transfer to dihaloaromatics.

2. Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

3. Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.

4. Unprecedented negishi coupling at C-br in the presence of a stannyl group as a convenient approach to pyridinylstannanes and their application in liquid crystal synthesis.

5. Transition-metal-catalyzed Suzuki-Miyaura cross-coupling reactions: a remarkable advance from palladium to nickel catalysts.

6. Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen.

7. Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: access to aryl/heteroarylethyloxy motifs.

8. A general solution for the 2-pyridyl problem.

9. Regioselective reactions of 3,4-pyridynes enabled by the aryne distortion model.

10. Stereospecific pd-catalyzed cross-coupling reactions of secondary alkylboron nucleophiles and aryl chlorides.

1. Photochemically Mediated Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamides.

2. Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters.