B(C 6 F 5 ) 3 -Catalyzed Chemical Tagging of Bioactive N -Alkylamines through β-Amino C(sp 3 )–H Functionalization
Year: 2026
Type: article
Abstract: We present a late-stage functionalization method for arming bioactive N -alkylamines with functional handles for bioconjugation through the transformations of β-amino C(sp 3 )–H bonds. B(C 6 F 5 ) 3 and a Brønsted base converts N -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.
Source: Organic Letters
Authors: Matthew Chapman, Changhang Dai, Yuankai Wang, Cunyuan Zhao, Quan Pham, Abhishek Chatterjee, Masayuki Wasa
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: G2965188289, G8067868759
OpenAlex ID: W7154207641