Reactivity of 3‐Substituted Fluorobenzenes in Palladium‐ Catalysed Direct Arylations with Aryl Bromides. Issue 7 (7th May 2014)

• Record Type: Journal Article
• Authors: Yan, Tao; Zhao, Liqin; He, Mian; Soulé, Jean‐François; Bruneau, Christian; Doucet, Henri
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 7(2014)
• Page Start: 1586
• Page End: 1596
• Publication Date: 2014-05-07
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201400038
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The influence of both electron‐withdrawing and electron‐donating substituents such as nitro, nitrile, chloro, bromo and methoxy at C‐3 on fluorobenzenes for their palladium‐catalysed direct C‐2 arylation has been explored. With electron‐withdrawing substituents, the reaction proceeds nicely using 2–4 mol% of an air‐stable palladium complex and potassium pivalate/dimethylacetamide (PivOK/DMA) as catalytic system; and in general, a very regioselective arylation at C‐2 was observed. Moreover, a variety of substituents on the aryl bromide coupling partner, such as benzoyl, formyl, nitro, nitrile, chloro and methyl, and also heteroaryl bromides were tolerated.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh5bw2qm" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>