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Mild Base Promoted Nucleophilic Substitution of Unactivated sp 3 ‐Carbon Electrophiles with Alkenylboronic Acids
Author(s) -
Liu Shiwen,
Zeng Xiaojun,
Hammond Gerald B.,
Xu Bo
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800826
Subject(s) - chemistry , electrophile , nucleophile , alkyl , nucleophilic substitution , transition metal , base (topology) , catalysis , carbon fibers , electrophilic substitution , substitution reaction , medicinal chemistry , base metal , organic chemistry , combinatorial chemistry , mathematical analysis , materials science , mathematics , composite number , composite material , welding , metallurgy
Diverse alkenylboronic acids react smoothly with various sp 3 ‐carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K 3 PO 4 . The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal‐free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling.