Two Directing Groups Used for Metal Catalysed Meta‐C−H Functionalisation Only Effect Ortho Electrophilic C−H Borylation
Sign Up to like & getrecommendations! Published in 2022 at "European Journal of Organic Chemistry"
DOI: 10.1002/ejoc.202200901
Abstract: Abstract Two templates used in meta‐directed C−H functionalisation under metal catalysis do not direct meta‐C−H borylation under electrophilic borylation conditions. Using BCl3 only Lewis adduct formation with Lewis basic sites in the template is observed.… read more here.
Keywords: meta borylation; ortho borylation; meta; borylation ... See more keywords
Construction of 1,2,3-Benzodiazaborole by Electrophilic Borylation of Azobenzene and Nucleophilic Dialkylative Cyclization.
Sign Up to like & getrecommendations! Published in 2021 at "Organic letters"
DOI: 10.1021/acs.orglett.1c03033
Abstract: 1,2,3-Benzodiazaboroles can be conveniently prepared from azobenzenes by a two-step protocol involving electrophilic ortho-borylation with BBr3 and dialkylative cyclization with the Grignard reagent. The methodology provides a diverse range of products equipped with functionalities from… read more here.
Keywords: cyclization; benzodiazaborole electrophilic; electrophilic borylation; dialkylative cyclization ... See more keywords
Electrophilic Borylation of Terminal Alkenes with BBr3/2,6-Disubstituted Pyridines.
Sign Up to like & getrecommendations! Published in 2018 at "Organic letters"
DOI: 10.1021/acs.orglett.8b00335
Abstract: A variety of terminal alkenes, as well as heteroaromatic compounds, are borylated by the combined use of BBr3/2,6-dichloropyridine (B3) or BBr3/2,6-lutidine (B5). α,α-Diarylalkenes prefer the former reagent combination, while other alkenes prefer the latter. Mechanistic… read more here.
Keywords: bbr3 disubstituted; terminal; borylation terminal; electrophilic borylation ... See more keywords
Enhanced N-directed electrophilic C–H borylation generates BN–[5]- and [6]helicenes with improved photophysical properties
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DOI: 10.1039/d1sc06513k
Abstract: Helicenes are chiral polycyclic aromatic hydrocarbons (PAHs) of significant interest, e.g. in supramolecular chemistry, materials science and asymmetric catalysis. Herein an enhanced N-directed electrophilic C–H borylation methodology has been developed that provides access to azaborine… read more here.
Keywords: enhanced directed; directed electrophilic; borylation generates; electrophilic borylation ... See more keywords
Amides as modifiable directing groups in electrophilic borylation
Sign Up to like & getrecommendations! Published in 2023 at "Chemical Science"
DOI: 10.1039/d2sc06483a
Abstract: Amide directed C–H borylation using ≥two equiv. of BBr3 forms borenium cations containing a R2N(R′)C Created by potrace 1.16, written by Peter Selinger 2001-2019 O→B(Ar)Br unit which has significant Lewis acidity at the carbonyl carbon.… read more here.
Keywords: 320 320; borylation reduction; borylation; amides modifiable ... See more keywords