Premium
Associative Covalent Relay: An Oxadiazolone Strategy for Rhodium(III)‐Catalyzed Synthesis of Primary Pyridinylamines
Author(s) -
Yu Xiaolong,
Chen Kehao,
Wang Qi,
Guo Shan,
Zha Shanke,
Zhu Jin
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201700320
Subject(s) - relay , rhodium , catalysis , associative property , covalent bond , formalism (music) , chemistry , combinatorial chemistry , physics , organic chemistry , mathematics , quantum mechanics , art , musical , power (physics) , pure mathematics , visual arts
A relay formalism is proposed herein for categorizing the interplay among reactants, target product, and catalytic center in transition‐metal catalysis, an important factor that can dictate overall catalysis viability and efficiency. In this formalism, transition‐metal catalysis can proceed by dissociative relay, associative covalent relay, and associative dative relay modes. An intriguing associative covalent relay process operates in rhodium(III)‐catalyzed oxadiazolone‐directed alkenyl C−H coupling with alkynes and allows efficient access to primary pyridinylamines. Although the primary pyridinylamine synthesis mechanism is posteriori rationalized, the relay formalism formulated herein can provide an important mechanistic conceptual framework for future catalyst design and reaction development.