Nickel-Catalyzed Synthesis of Benzylamines from (Hetero)aryl Halides and Glycine-Derived N-Hydroxyphthalimide Esters-Reference-Cited by-同舟云学术

Nickel-Catalyzed Synthesis of Benzylamines from (Hetero)aryl Halides and Glycine-Derived N-Hydroxyphthalimide Esters

Published:2024-01-12 Issue: Volume: Page:
ISSN:0936-5214
Container-title:Synlett
language:en
Short-container-title:Synlett

Author:

Huestis Malcolm P.¹^ORCID,Choi Eun Seo¹²,Rousseaux Sophie A. L.²^ORCID

Affiliation:

1. Discovery Chemistry, Genentech, Inc.

2. Davenport Research Laboratories, Department of Chemistry, University of Toronto

Abstract

AbstractA nickel-catalyzed aminomethylation of aryl or heteroaryl iodides or bromides for the preparation of protected primary benzylamines is reported. This cross-electrophile reductive protocol engages carbamate-protected, glycine-derived N-hydroxyphthalimide (NHP) esters in an efficient decarboxylative cross-coupling in only two hours. The catalyst and NHP ester reagents are commercially available or can be synthesized in one step on a decagram scale with no chromatography.

Funder

University of Toronto

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0043-1763656.pdf

Reference24 articles.

1. Recent developments and perspectives in palladium-catalyzed cyanation of aryl halides: synthesis of benzonitriles

2. Reduction of organic compounds with sodium borohydride-transition metal salt systems

3. Synthesis and Suzuki–Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides

4. One-Pot Primary Aminomethylation of Aryl and Heteroaryl Halides with Sodium Phthalimidomethyltrifluoroborate

5. Suzuki–Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Mesylates