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. 2022 Apr 14;58(31):4869-4872.
doi: 10.1039/d2cc00425a.

Decatungstate-photocatalysed C(sp3)-H azidation

Yen-Chu Lu  1 , Shih-Chieh Kao  1 , Julian G West  1
Affiliations

Decatungstate-photocatalysed C(sp3)-H azidation

Yen-Chu Lu et al. Chem Commun (Camb). .

Abstract

C-H Azidation is an increasingly important tool for bioconjugation, materials chemistry, and the synthesis of nitrogen-containing natural products. While several approaches have been developed, these often require exotic and energetic reagents, expensive photocatalysts, or both. Here we report a simple and general C-H azidation reaction using earth-abundant tetra-n-butylammonium decatungstate as a photocatalyst and commercial p-acetamidobenzenesulfonyl azide (p-ABSA) as the azide source. This system can azidate a variety of unactivated C(sp3)-H bonds in moderate to good yields and excellent turnover numbers. Preliminary mechanistic experiments implicate a radical mechanism proceeding VIA photo-hydrogen atom transfer (photo-HAT).

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Conflict of interest statement

Conflicts of interest

There are no conflicts to declare.

Figures

Figure 1.
Figure 1.
Photocatalysed C(sp3)–H Azidation Strategies
Figure 2.
Figure 2.
TEMPO experiment on TBADT-catalysed C(sp3)–H azidation
Figure 3.
Figure 3.
Proposed mechanism of TBADT-catalysed C(sp3)-H azidation
See this image and copyright information in PMC

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