A General and Practical Palladium‐Catalyzed Direct α‐Arylation of Amides with Aryl Halides. Issue 1 (10th January 2014)

• Record Type: Journal Article
• Authors: Zheng, Bing; Jia, Tiezheng; Walsh, Patrick J.
• Is Part Of: Advanced synthesis & catalysis. Volume 356:Issue 1(2014)
• Page Start: 165
• Page End: 178
• Publication Date: 2014-01-10
• 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.201300851
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>An efficient system for the direct catalytic intermolecular α‐arylation of acetamide derivatives with aryl bromides and chlorides is presented. The palladium catalyst is supported by Kwong's indole‐based phosphine ligand and provides monoarylated amides in up to 95% yield. Excellent chemoselectivities (&gt;10:1) in the mono‐ and diarylation with aryl bromides were achieved by careful selection of bases, solvents, and stoichiometry. Under the coupling conditions, the weakly acidic α‐protons of amides (p<italic>K</italic>_a up to 35) were reversibly depotonated by lithium <italic>tert</italic>‐butoxide (LiO‐<italic>t‐</italic>Bu), sodium <italic>tert</italic>‐butoxide (NaO‐<italic>t‐</italic>Bu) or sodium bis(trimethylsilyl)amide [NaN(SiMe₃)₂].</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgg4sm4915z" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>