Pd(II)-Catalyzed Csp<sup>2</sup>–H Carbonylative Amidation of Groebke–Blackburn–Bienaymé Reaction Products: Access to Imidazo[1,2-<i>a</i>]pyridine-Fused δ-Lactams
The Groebke-Blackburn-Bienaymé (GBB) reaction provides efficient access to imidazole-fused heterocycles, yet it is inevitably endowed with an isocyanide-derived secondary amino group in products. Herein, we report a Pd(II)-catalyzed sp<sup>2</sup> C-H carbonylative amidation strategy using Co<sub>2</sub>(CO)<sub>8</sub> as a safe CO surrogate. Leveraging the native aryl amino group as a directing motif, this protocol enables direct conversion of GBB adducts into pharmaceutically relevant imidazo[1,2-<i>a</i>]pyridine-fused δ-lactams with up to 86% yield. The method demonstrates exceptional functional group tolerance and eliminates prefunctionalization requirements, offering a streamlined approach to access complex nitrogen-rich architectures.
Authors
- Xingang Xie (ORCID: https://orcid.org/0000-0002-0707-1229)
- Wen Qin (ORCID: https://orcid.org/0000-0002-2714-3613)
- Lingmeng Xie (ORCID: https://orcid.org/0009-0005-4641-561X)
- Xing Huo (ORCID: https://orcid.org/0000-0001-8527-5975)
- Jingru Zou
Institutions
- State Key Laboratory of Chemical Engineering (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-09-13
- DOI
- https://doi.org/10.1021/acs.joc.5c01662
- Primary Topic
- Nanomaterials for catalytic reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.00