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Microwave-mediated Synthesis of an Arylboronate Library

Microwave-mediated Synthesis of an Arylboronate Library

John Spencer, Christine B Baltus, Hiren Patel, Neil J Press, Samantha K Callear, Louise Male, Simon J Coles

ACS Comb Sci. 2011 Jan 10;13(1):24-31.

PMID: 21247121

Abstract:

A series of arylboronates has been synthesized from the reaction of 2-(2-, (3-, or (4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 1{1-3} respectively with a range of N-, S-, and O-nucleophiles, using microwave-mediated chemistry. For the synthesis of N- and S-substituted boronates, a supported base, PS-NMM, was employed, and many reactions were complete within 15 min. With O-nucleophiles, a mixture of tetrabutylammonium bromide, potassium carbonate, and sodium hydroxide was employed. The resulting aminomethyl, mercaptomethyl, or alkoxy-/phenoxymethyl-arylboronates were subjected to microwave-mediated Suzuki Miyaura coupling reactions to afford a range of biaryls in moderate to good yields. The X-ray structures of five boronates were determined.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS793384	2-[3-([1,3]dioxolan-2-ylmethoxy)-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane			Price

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