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Literature DB >> 22206416

Heterocycle synthesis via direct C-H/N-H coupling.

Abstract

A method for five- and six-membered heterocycle formation by class="Chemical">palladium-catalyzed C-H/N-H coupling is presented. The method employs a <class="Chemical">span class="Chemical">picolinamide directing group, PhI(OAc)(2) oxidant, and toluene solvent at 80-120 °C. Cyclization is effective for sp(2) as well as aliphatic and benzylic sp(3) C-H bonds.

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Year: 2011 PMID： 22206416 PMCID： PMC3257368 DOI： 10.1021/ja210959p

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

38 in total

1. Auxiliary-assisted palladium-catalyzed arylation and alkylation of sp2 and sp3 carbon-hydrogen bonds.

Authors: Dmitry Shabashov; Olafs Daugulis
Journal: J Am Chem Soc Date: 2010-03-24 Impact factor: 15.419

2. Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

Authors: B V Subba Reddy; Leleti Rajender Reddy; E J Corey
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

Review 3. Aryl-aryl bond formation by transition-metal-catalyzed direct arylation.

Authors: Dino Alberico; Mark E Scott; Mark Lautens
Journal: Chem Rev Date: 2007-01 Impact factor: 60.622

4. Pd-catalyzed intramolecular oxidative C-H amination: synthesis of carbazoles.

Authors: So Won Youn; Joon Hyung Bihn; Byung Seok Kim
Journal: Org Lett Date: 2011-06-14 Impact factor: 6.005

5. Functionalization of organic molecules by transition-metal-catalyzed C(sp3)-H activation.

Authors: Rodolphe Jazzar; Julien Hitce; Alice Renaudat; Julien Sofack-Kreutzer; Olivier Baudoin
Journal: Chemistry Date: 2010-03-01 Impact factor: 5.236

6. Scope and mechanism of allylic C-H amination of terminal alkenes by the palladium/PhI(OPiv)2 catalyst system: insights into the effect of naphthoquinone.

Authors: Guoyin Yin; Yichen Wu; Guosheng Liu
Journal: J Am Chem Soc Date: 2010-09-01 Impact factor: 15.419

7. High-yielding palladium-catalyzed intramolecular alkane arylation: reaction development and mechanistic studies.

Authors: Marc Lafrance; Serge I Gorelsky; Keith Fagnou
Journal: J Am Chem Soc Date: 2007-11-07 Impact factor: 15.419

8. Delta and alpha SP(3) C-H bond oxidation of sulfonamides with PhI(OAc)(2)/I(2) under metal-free conditions.

Authors: Renhua Fan; Dongming Pu; Fengqi Wen; Jie Wu
Journal: J Org Chem Date: 2007-10-11 Impact factor: 4.354

9. Catalytic asymmetric allylic and homoallylic diamination of terminal olefins via formal C-H activation.

Authors: Haifeng Du; Baoguo Zhao; Yian Shi
Journal: J Am Chem Soc Date: 2008-06-13 Impact factor: 15.419

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors: Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

41 in total

1. Heterocycle Formation via Palladium-Catalyzed C-H Functionalization.

Authors: Tian-Sheng Mei; Lei Kou; Sandy Ma; Keary M Engle; Jin-Quan Yu
Journal: Synthesis (Stuttg) Date: 2012-05-25 Impact factor: 3.157

2. Intermolecular Ritter-type C-H amination of unactivated sp3 carbons.

Authors: Quentin Michaudel; Damien Thevenet; Phil S Baran
Journal: J Am Chem Soc Date: 2012-01-27 Impact factor: 15.419

3. Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

Authors: Ru-Yi Zhu; Keita Tanaka; Gen-Cheng Li; Jian He; Hai-Yan Fu; Su-Hua Li; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-05-27 Impact factor: 15.419

4. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

Review 5. Hypervalent Iodine Reagents in High Valent Transition Metal Chemistry.

Authors: Felipe Cesar Sousa E Silva; Anthony F Tierno; Sarah E Wengryniuk
Journal: Molecules Date: 2017-05-12 Impact factor: 4.411

6. Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C-H Bonds.

Authors: Kyle Clagg; Haiyun Hou; Adam B Weinstein; David Russell; Shannon S Stahl; Stefan G Koenig
Journal: Org Lett Date: 2016-07-12 Impact factor: 6.005

7. C-H activation: the road less travelled to amination.

Authors: Olga V Zatolochnaya; Vladimir Gevorgyan
Journal: Nat Chem Date: 2014-08 Impact factor: 24.427

8. Scope and limitations of auxiliary-assisted, palladium-catalyzed arylation and alkylation of sp2 and sp3 C-H bonds.

Authors: Enrico T Nadres; Gerson Ivan Franco Santos; Dmitry Shabashov; Olafs Daugulis
Journal: J Org Chem Date: 2013-09-19 Impact factor: 4.354

9. Iridium-Catalyzed, β-Selective C(sp³)-H Silylation of Aliphatic Amines To Form Silapyrrolidines and 1,2-Amino Alcohols.

Authors: Bo Su; Taegyo Lee; John F Hartwig
Journal: J Am Chem Soc Date: 2018-12-13 Impact factor: 15.419

10. Directed amination of non-acidic arene C-H bonds by a copper-silver catalytic system.

Authors: Ly Dieu Tran; James Roane; Olafs Daugulis
Journal: Angew Chem Int Ed Engl Date: 2013-04-24 Impact factor: 15.336