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Diversity‐Oriented Synthesis of α‐Functionalized Acylborons and Borylated Heteroarenes by Nucleophilic Ring Opening of α‐Chloroepoxyboronates
Author(s) -
Tan DongHang,
Cai YuanHong,
Zeng YaoFu,
Lv WenXin,
Yang Ling,
Li Qingjiang,
Wang Honggen
Publication year - 2019
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.201907349
Subject(s) - synthon , nucleophile , chemistry , ring (chemistry) , functional group , combinatorial chemistry , modular design , organic chemistry , computer science , catalysis , polymer , operating system
The ring‐opening reactions of N ‐methyliminodiacetyl (MIDA) α‐chloroepoxyboronates with different nucleophiles allow the modular synthesis of a diverse array of organoboronates. These include seven types of α‐functionalized acylboronates and seven types of borylated heteroarenes, some of which are difficult‐to‐access products using alternative methods. The common synthons, α‐chloroepoxyboronates, could be viably synthesized by a two‐step procedure from the corresponding alkenyl MIDA boronates. Mild reaction conditions, good functional‐group tolerance, and generally good efficiency were observed. The utility of the products was also demonstrated.