Synthesis 2024; 56(21): 3261-3276
DOI: 10.1055/a-2182-7416
paper
Special Issue PSRC-10 (10th Pacific Symposium on Radical Chemistry)

Photoinduced Alkylation of Diazines with N-(Acyloxy)phthalimides in the Presence of Triethylamine

Itziar Guerrero
a   School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
,
Eugene Yew Kun Tan
a   School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
,
Yuliang Liu
a   School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
,
Lee J. Edwards 
b   Drug Substance Development, GlaxoSmithKline, Gunnels Wood Road, Stevenage, SG1 2NY, UK
,
Shunsuke Chiba  ∗
a   School of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
› Author AffiliationsThis work was supported by funding from Nanyang Technological University (NTU), GlaxoSmithKline (REQ0315299), and the Ministry of Education – Singapore (Academic Research Fund Tier 2: MOE-T2EP10122-0007).
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Dedicated to Professor Shigeru Yamago on the occasion of his 60th birthday

Abstract

A photochemical protocol for the alkylation of diazines (pyrimidines, pyrazines, and pyridazines) with N-(acyloxy)phthalimides has been developed. The process is facilitated by the presence of triethylamine under irradiation with 427–390 nm light; this enables rapid cross-coupling reactions to construct a wide range of alkylated diazines.

Key words

N-(acyloxy)phthalimides - diazines - radicals - electron donor–acceptor (EDA) complexes - Minisci-type alkylation

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2182-7416.
  • Supporting Information


Publication History

Received: 06 September 2023

Accepted after revision: 27 September 2023

Accepted Manuscript online:
27 September 2023

Article published online:
06 November 2023

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