Literature DB >> 23750615

Palladium-catalyzed direct C-H arylation of cyclic enaminones with aryl iodides.

Yi-Yun Yu1, Lei Bi, Gunda I Georg.   

Abstract

A ligand-free method for the Pd-catalyzed direct arylation of cyclic enaminones using aryl iodides was developed. This method can be applied to a wide range of cyclic enaminones and aryl iodides with excellent C5-regioselectivity. Using widely available aryl iodides, the generality of this transformation provides easy access to a variety of 3-arylpiperidine structural motifs.

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Year:  2013        PMID： 23750615      PMCID： PMC3767375          DOI： 10.1021/jo400830t

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  33 in total

1.  Direct Hiyama cross-coupling of enaminones with triethoxy(aryl)silanes and dimethylphenylsilanol.

Authors:  Lei Bi; Gunda I Georg
Journal:  Org Lett       Date:  2011-09-22       Impact factor: 6.005

2.  Cobalt-catalyzed ortho-arylation of aromatic imines with aryl chlorides.

Authors:  Ke Gao; Pin-Sheng Lee; Chong Long; Naohiko Yoshikai
Journal:  Org Lett       Date:  2012-08-08       Impact factor: 6.005

Review 3.  Towards mild metal-catalyzed C-H bond activation.

Authors:  Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal:  Chem Soc Rev       Date:  2011-06-10       Impact factor: 54.564

4.  Beyond directing groups: transition-metal-catalyzed C-H activation of simple arenes.

Authors:  Nadine Kuhl; Matthew N Hopkinson; Joanna Wencel-Delord; Frank Glorius
Journal:  Angew Chem Int Ed Engl       Date:  2012-09-20       Impact factor: 15.336

5.  Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

6.  Ligand-accelerated Pd-catalyzed ketone γ-arylation via C-C cleavage with aryl chlorides.

Authors:  Asraa Ziadi; Ruben Martin
Journal:  Org Lett       Date:  2012-02-14       Impact factor: 6.005

7.  Synthesis of the quinolizidine alkaloids (-)-lasubine II and (+/-)-myrtine by conjugate addition and intramolecular acylation of amino esters with acetylenic sulfones.

Authors:  Thomas G Back; Michael D Hamilton; Vania J J Lim; Masood Parvez
Journal:  J Org Chem       Date:  2005-02-04       Impact factor: 4.354

8.  Palladium(II)-catalyzed dehydrogenative alkenylation of cyclic enaminones via the Fujiwara-Moritani reaction.

Authors:  Yi-Yun Yu; Micah J Niphakis; Gunda I Georg
Journal:  Org Lett       Date:  2011-10-13       Impact factor: 6.005

9.  Transition metal-catalyzed direct arylation of substrates with activated sp3-hybridized C-H bonds and some of their synthetic equivalents with aryl halides and pseudohalides.

Authors:  Fabio Bellina; Renzo Rossi
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

10.  Two methods for direct ortho-arylation of benzoic acids.

Authors:  Hendrich A Chiong; Quynh-Nhu Pham; Olafs Daugulis
Journal:  J Am Chem Soc       Date:  2007-07-25       Impact factor: 15.419
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  5 in total

1.  Regioselective C5-alkylation and C5-methylcarbamate formation of 2,3-dihydro-4-pyridones and C3-alkylation and C3-methylcarbamate formation of 4-(pyrrolidin-1-yl)furan-2(5H)-one.

Authors:  Xingxian Gu; Gunda I Georg
Journal:  Tetrahedron Lett       Date:  2015-10-21       Impact factor: 2.415

2.  Biomimetic Aerobic C-H Olefination of Cyclic Enaminones at Room Temperature: Development toward the Synthesis of 1,3,5-Trisubstituted Benzenes.

Authors:  Yi-Yun Yu; Gunda I Georg
Journal:  Adv Synth Catal       Date:  2014-04-14       Impact factor: 5.837

3.  Boron-Heck reaction of cyclic enaminones: regioselective direct arylation via oxidative palladium(II) catalysis.

Authors:  Yong Wook Kim; Gunda I Georg
Journal:  Org Lett       Date:  2014-03-03       Impact factor: 6.005

4.  Unraveling innate substrate control in site-selective palladium-catalyzed C-H heterocycle functionalization.

Authors:  Hwanho Choi; Minsik Min; Qian Peng; Dahye Kang; Robert S Paton; Sungwoo Hong
Journal:  Chem Sci       Date:  2016-03-08       Impact factor: 9.825

5.  Palladium-catalyzed direct arylation of 5-halouracils and 5-halouracil nucleosides with arenes and heteroarenes promoted by TBAF.

Authors:  Yong Liang; Jennifer Gloudeman; Stanislaw F Wnuk
Journal:  J Org Chem       Date:  2014-04-23       Impact factor: 4.354
  5 in total

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