Literature DB >> 20812741

Direct C-H arylation of electron-deficient heterocycles with arylboronic acids.

Ian B Seiple1, Shun Su, Rodrigo A Rodriguez, Ryan Gianatassio, Yuta Fujiwara, Adam L Sobel, Phil S Baran.   

Abstract

A direct arylation of a variety of electron-deficient heterocycles with arylboronic acids has been developed. This new reaction proceeds readily at room temperature using inexpensive reagents: catalytic silver(I) nitrate in the presence of persulfate co-oxidant. The scope with respect to heterocycle and boronic acid coupling partner is broad, and sensitive functional groups are tolerated. This method allows for rapid access to a variety of arylated heterocycles that would be more difficult to access with traditional methods.

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Year:  2010        PMID: 20812741      PMCID: PMC2946225          DOI: 10.1021/ja1066459

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  13 in total

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Journal:  J Am Chem Soc       Date:  2008-10-15       Impact factor: 15.419

7.  Palladium-catalyzed direct arylation of azine and azole N-oxides: reaction development, scope and applications in synthesis.

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Journal:  J Am Chem Soc       Date:  2009-03-11       Impact factor: 15.419

8.  Palladium-catalyzed direct C-2 arylation of indoles with potassium aryltrifluoroborate salts.

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Journal:  J Org Chem       Date:  2008-08-15       Impact factor: 4.354

9.  Establishment of broadly applicable reaction conditions for the palladium-catalyzed direct arylation of heteroatom-containing aromatic compounds.

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10.  Total synthesis of palau'amine.

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  72 in total

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Journal:  J Am Chem Soc       Date:  2011-09-22       Impact factor: 15.419

2.  Innate and guided C-H functionalization logic.

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4.  Oxidative Generation of Boron-Centered Radicals in Carboranes.

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Review 5.  Is there no end to the total syntheses of strychnine? Lessons learned in strategy and tactics in total synthesis.

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6.  Catalytic Radical Domino Reactions in Organic Synthesis.

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7.  Chichibabin-type direct alkylation of pyridyl alcohols with alkyl lithium reagents.

Authors:  Jenna L Jeffrey; Richmond Sarpong
Journal:  Org Lett       Date:  2012-10-12       Impact factor: 6.005

8.  Uncovering the mechanism of the Ag(I)/persulfate-catalyzed cross-coupling reaction of arylboronic acids and heteroarenes.

Authors:  Niki R Patel; Robert A Flowers
Journal:  J Am Chem Soc       Date:  2013-03-18       Impact factor: 15.419

9.  The Pyridyldiisopropylsilyl Group: A Masked Functionality and Directing Group for Monoselective ortho-Acyloxylation and ortho-Halogenation Reactions of Arenes.

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10.  Synthesis and minisci reactions of organotrifluoroborato building blocks.

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