Nickel-Catalyzed Deallylation for Sustainable Solution and Solid-Phase Peptide Synthesis

Organic Letters 2026

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Authors: Maria Camila Aguilera, Steven W. M. Crossley, Renee J. Sifri, Kyle E. Ruhl, Serge Ruccolo, Yangzhong Qin, Brittany M. Armstrong, Omer Ad
DOI: 10.1021/acs.orglett.6c00213
Cited by: 2
References: 39

Abstract

We report a one-step, nickel-catalyzed allyl/alloc deprotection compatible with solid-phase peptide synthesis (SPPS) to address the reliance on costly palladium conditions and limited on-resin compatibility of base-metal alternatives. Our two-component system employs an air-stable Ni(PPh 3 ) 2 Br 2 precatalyst and NH 3 BH 3 reductant and operates rapidly in SPPS-compatible solvents under inertion. This protocol efficiently and chemoselectively deprotects allyl- and alloc-protected amino acids, small molecules, and peptides in solution and has been extended to on-resin deprotection, showing promise for SPPS applications.

Fields of Study & Subjects

Chemical Synthesis and Analysis Supramolecular Self-Assembly in Materials Click Chemistry and Applications

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
9
Pages
2965–2970
Publication date
25 February 2026
Language
EN