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DOI: 10.1055/s-0043-1763656
Nickel-Catalyzed Synthesis of Benzylamines from (Hetero)aryl Halides and Glycine-Derived N-Hydroxyphthalimide Esters
S.A.L.R. thanks NSERC (Discovery Grant and Canada Research Chair programs) and the University of Toronto for financial support.
Dedicated to the late Prof. Keith Fagnou on the 20th anniversary of the start of his academic career.
Abstract
A 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.
Key words
cross-electrophile - glycine - hydroxyphthalimide esters - decarboxylative cross-coupling - aminomethylation - benzylaminesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0043-1763656.
- Supporting Information
Publication History
Received: 27 September 2023
Accepted after revision: 21 November 2023
Article published online:
12 January 2024
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References and Notes
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Dual photoredox/Ni-catalyzed alkylations of aryl halides using aminomethyl silanes and potassium aminomethyl trifluoroborate salts function with tertiary N-Boc-amines and thus cannot afford primary benzyl amines, see: