Regiospecific synthesis of functionalised 1,3-diarylisobenzofurans viapalladium- and rhodium-catalysed reaction of boronic acids with o-acylbenzaldehydes under thermal or microwave activation

Literature Information

Publication Date 2010-08-26
DOI 10.1039/C0OB00110D
Impact Factor 3.876
Authors

Jérôme Jacq, Bernard Bessières, Cathy Einhorn, Jacques Einhorn


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Abstract

Variously substituted 1,3-diarylisobenzofurans have been regiospecifically prepared via palladium- and rhodium-catalysed reaction of functionalised boronic acids onto o-acylbenzaldehydes. Rhodium catalysis has furthermore been improved using microwave activation. Thus, isobenzofurans containing aryl groups substituted by halogens, unprotected amine, alcohol and even aldehyde groups, have been obtained directly in good to satisfactory yields. Divergent results have been observed when palladium-, rhodium- and MW-activated rhodium-catalysis was applied to the reaction of phenylboronic acid with an iodinated o-acylbenzaldehyde, leading principally to Suzuki coupling product and/or to iodinated isobenzofuran.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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