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Pd‐Catalyzed Amination of Functionalized 6‐Bromo‐pyridinyl‐1,2,4‐triazine Complexant Scaffolds
Author(s) -
Cleveland Jacob W.,
Carrick Jesse D.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700585
Subject(s) - chemistry , amination , catalysis , triazine , combinatorial chemistry , polymer chemistry , 1,3,5 triazine , organic chemistry , medicinal chemistry
Current efforts in this laboratory continue to focus on the preparation of novel complexant motifs for potential use in chemoselective minor‐actinide liquid–liquid separations of relevant cations from used nuclear fuel. The present work describes an efficient Pd‐catalyzed amination reaction of diversely functionalized 6‐bromo‐1,2,4‐triazinyl‐pyridine scaffolds with various amines to afford the opportunity for convergent modulation of complexant electronic and steric properties directly from one substrate towards potentially enhanced solubility in process‐relevant solvents. The 21 novel examples presented highlight a unified approach to extensive molecular diversity and provide the ability to further study chelate effects, solubility properties, and complexation efficacy on nonsymmetric, moderately soft‐Lewis‐basic complexant scaffolds without the incorporation of additional heteroaromatic moieties. Synthetic‐method optimization, amine and scaffold scope, as well as a scale‐up experiment are presented.