452972-11-1

Usage

Uses

2-Chloropyridine-3-boronic acid, pinacol ester

InChI:InChI=1/C11H15BClNO2/c1-10(2)11(3,4)16-12(15-10)8-6-5-7-14-9(8)13/h5-7H,1-4H3

Upstream product

• 109-09-1 2-chloropyridine 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 52200-48-3 3-bromo-2-chloropyridine 
• 78607-36-0 2-chloro-3-iodopyridine 
• 381248-04-0 (2-chloropyridin-3-yl)boronic acid 

Downstream Products

• 6636-78-8 2-chloro-3-hydroxypyridine 
• 1426414-39-2 (R)-2-chloro-3-(1-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)pyridine 
• 1426414-42-7 (S)-1-(2-chloropyridin-3-yl)-1-phenylethanol 
• 1426414-53-0 (R)-2-chloro-3-(1-phenylethyl)pyridine 
• 924312-01-6 3-[4(trifluoromethoxy)phenoxy]pyridin-2(1H)-one 

Relevant academic research and scientific papers

Asymmetric synthesis of 1-heteroaryl-1-arylalkyl tertiary alcohols and 1-pyridyl-1-arylethanes by lithiation-borylation methodology

The synthesis of highly enantioenriched α-heterocyclic tertiary alcohols has been achieved via lithiation-borylation of a configurationally stable lithiated carbamate and heterocyclic pinacol boronic esters followed by oxidation. Protodeboronation of the α-heterocyclic tertiary boronic esters using TBAF·3H2O or CsF gave highly enantioenriched 1-pyridyl-1-arylethanes in high er.

Synthesis of novel halopyridinylboronic acids and esters. Part 2: 2,4, or 5-Halopyridin-3-yl-boronic acids and esters

This paper describes a general method for the synthesis and the isolation of novel 2,4, or 5-halopyridin-3-yl-boronic acids and esters 4, 7, 10, 13, 15. These compounds are prepared taking into account a regioselective halogen-metal exchange using nBuLi or a regioselective ortho-lithiation using lithium diisopropylamide and subsequent quenching with triisopropylborate starting from appropriate mono or dihalopyridines. All substrates studied to date provided a single regioisomeric boronic acid or ester product. Additionally, these compounds have been found to undergo Pb-catalyzed coupling with a range of arylhalides and authorize a strategy to produce new pyridines libraries.