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C-H Borylation Catalysts That Distinguish Between Similarly Sized Substituents Like Fluorine and Hydrogen

C-H Borylation Catalysts That Distinguish Between Similarly Sized Substituents Like Fluorine and Hydrogen

Susanne L Miller, Ghayoor A Chotana, Jonathan A Fritz, Buddhadeb Chattopadhyay, Robert E Maleczka Jr, Milton R Smith 3rd

Org Lett. 2019 Aug 16;21(16):6388-6392.

PMID: 31393137

Abstract:

By modifying ligand steric and electronic profiles it is possible to C-H borylate ortho or meta to substituents in aromatic and heteroaromatic compounds, where steric differences between accessible C-H sites are small. Dramatic effects on selectivities between reactions using B2pin2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) are described for the first time. Judicious ligand and borane combinations give highly regioselective C-H borylations on substrates where typical borylation protocols afford poor selectivities.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS793324	2-(3,4-dimethoxyloxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane			Price

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