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Literature DB >> 31909622

Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp³) Electrophiles: Reaction Development and Application to Targets of Interest.

Seung Moh Koo¹, Alex J Vendola¹, Sarah Noemi Momm¹, James P Morken¹.

Abstract

A catalytic conjunctive cross-coupling reaction is developed that allows the construction of chiral organoboronic esters from alkylboron ate complexes and alkyl iodide electrophiles. The process occurs most efficiently with a Ni/Pybox-comprised catalyst and with an acenapthoquinone-derived boron ligand. Because of the broad functional group tolerance of this reaction, it can be a versatile tool for organic synthesis. Applications to the construction of (R)-coniine and (-)-indolizidine 209D are described.

Entities: Chemical Species

Mesh：

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Year: 2020 PMID： 31909622 PMCID： PMC7054899 DOI： 10.1021/acs.orglett.9b04453

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

43 in total

1. A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams.

Authors: Mark Daly; Kathryn Gill; Mairi Sime; Graham L Simpson; Andrew Sutherland
Journal: Org Biomol Chem Date: 2011-08-12 Impact factor: 3.876

2. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

Authors: Liang Zhang; Gabriel J Lovinger; Emma K Edelstein; Adam A Szymaniak; Matteo P Chierchia; James P Morken
Journal: Science Date: 2016-01-01 Impact factor: 47.728

3. Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling.

Authors: Joseph Derosa; Van T Tran; Mark N Boulous; Jason S Chen; Keary M Engle
Journal: J Am Chem Soc Date: 2017-07-28 Impact factor: 15.419

Review 4. The versatility of boron in biological target engagement.

Authors: Diego B Diaz; Andrei K Yudin
Journal: Nat Chem Date: 2017-07-25 Impact factor: 24.427

5. Mn-mediated coupling of alkyl iodides and chiral N-acylhydrazones: optimization, scope, and evidence for a radical mechanism.

Authors: Gregory K Friestad; Jean-Charles Marié; YoungSung Suh; Jun Qin
Journal: J Org Chem Date: 2006-09-01 Impact factor: 4.354

6. Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Authors: Emma K Edelstein; Sheila Namirembe; James P Morken
Journal: J Am Chem Soc Date: 2017-03-29 Impact factor: 15.419

Alkyl Group Migration in Ni-Catalyzed Conjunctive Coupling with C(sp³) Electrophiles: Reaction Development and Application to Targets of Interest.

1. A new general approach for the stereocontrolled synthesis of functionalised γ- and δ-lactams.

2. Catalytic conjunctive cross-coupling enabled by metal-induced metallate rearrangement.

3. Nickel-Catalyzed β,γ-Dicarbofunctionalization of Alkenyl Carbonyl Compounds via Conjunctive Cross-Coupling.

Review 4. The versatility of boron in biological target engagement.

5. Mn-mediated coupling of alkyl iodides and chiral N-acylhydrazones: optimization, scope, and evidence for a radical mechanism.

6. Enantioselective Conjunctive Cross-Coupling of Bis(alkenyl)borates: A General Synthesis of Chiral Allylboron Reagents.

Review 7. Asymmetric Synthesis of Secondary and Tertiary Boronic Esters.

8. Nickel-Catalyzed 1,2-Diarylation of Simple Alkenyl Amides.

9. Fast Diazaborine Formation of Semicarbazide Enables Facile Labeling of Bacterial Pathogens.

10. Direct stereospecific amination of alkyl and aryl pinacol boronates.

1. Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters.