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

Itziar Guerrero; Eugene Yew Kun Tan; Yuliang Liu; Lee J. Edwards; Shunsuke Chiba

doi:10.1055/a-2182-7416

Synthesis, Table of Contents

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

Authors

Itziar Guerrero

^aSchool of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
Eugene Yew Kun Tan

^aSchool of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
Yuliang Liu

^aSchool of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore
Lee J. Edwards

^bDrug Substance Development, GlaxoSmithKline, Gunnels Wood Road, Stevenage, SG1 2NY, UK
Shunsuke Chiba ∗

^aSchool of Chemistry, Chemical Engineering and Biotechnology, Nanyang Technological University, Singapore 637371, Singapore

Abstract

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Dedicated to Professor Shigeru Yamago on the occasion of his 60^th 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

Full Text

References

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Supplementary Material

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