B(C <sub>6</sub> F <sub>5</sub> ) <sub>3</sub> -Catalyzed Chemical Tagging of Bioactive <i>N</i> -Alkylamines through β-Amino C(sp <sup>3</sup> )–H Functionalization
-alkylamines into enamines through sequential hydride abstraction and deprotonation. The resulting enamines, generated in situ, undergo conjugate addition to maleimide-based tagging agents to furnish β-substituted amine derivatives bearing diverse bioconjugation handles. These transformations proceed under redox-neutral conditions and tolerate a range of Lewis acid-sensitive moieties.
Authors
- Changhang Dai
- Abhishek Chatterjee (ORCID: https://orcid.org/0000-0002-6231-5302)
- 赵存元
- Matthew Chapman (ORCID: https://orcid.org/0000-0001-6449-217X)
- Masayuki Wasa (ORCID: https://orcid.org/0000-0002-3309-9129)
- Yuankai Wang
- Quan Pham
Institutions
- Boston College (US)
- Merck & Co., Inc., Rahway, NJ, USA (United States) (US)
- Scripps Institution of Oceanography (US)
- Scripps (United States) (US)
- The Herbert Wertheim UF Scripps Institute for Biomedical Innovation & Technology
- University of Montana (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2026-04-14
- DOI
- https://doi.org/10.1021/acs.orglett.6c01364
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Institute of General Medical Sciences