Literature DB >> 21082838

Pd(II)-catalyzed carbonylation of C(sp3)-H bonds: a new entry to 1,4-dicarbonyl compounds.

Eun Jeong Yoo1, Masayuki Wasa, Jin-Quan Yu.   

Abstract

Pd(II)-catalyzed β-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing α-hydrogen atoms and could be applied to effect methylene C(sp(3))-H carbonylation of cyclopropanes.

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Year:  2010        PMID： 21082838      PMCID： PMC3135760          DOI： 10.1021/ja108754f

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


  26 in total

1.  From noble metal to Nobel Prize: palladium-catalyzed coupling reactions as key methods in organic synthesis.

Authors:  Xiao-Feng Wu; Pazhamalai Anbarasan; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-22       Impact factor: 15.336

2.  Palladium-catalyzed asymmetric iodination of unactivated C-H bonds under mild conditions.

Authors:  Ramesh Giri; Xiao Chen; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2005-03-29       Impact factor: 15.336

3.  Palladium-catalyzed oxidative ethoxycarbonylation of aromatic C-H bond with diethyl azodicarboxylate.

Authors:  Wing-Yiu Yu; Wing Nga Sit; Kin-Man Lai; Zhongyuan Zhou; Albert S C Chan
Journal:  J Am Chem Soc       Date:  2008-02-26       Impact factor: 15.419

4.  Enantioselective organocatalytic singly occupied molecular orbital activation: the enantioselective alpha-enolation of aldehydes.

Authors:  Hye-Young Jang; Jun-Bae Hong; David W C MacMillan
Journal:  J Am Chem Soc       Date:  2007-05-12       Impact factor: 15.419

5.  Pyrrolidinedione derivatives as antibacterial agents with a novel mode of action.

Authors:  Jens Pohlmann; Thomas Lampe; Mitsuyuki Shimada; Peter G Nell; Josef Pernerstorfer; Niels Svenstrup; Nina A Brunner; Guido Schiffer; Christoph Freiberg
Journal:  Bioorg Med Chem Lett       Date:  2005-02-15       Impact factor: 2.823

6.  Preparation of benzolactams by Pd(OAc)2-catalyzed direct aromatic carbonylation.

Authors:  Kazuhiko Orito; Akiyoshi Horibata; Takatoshi Nakamura; Harumi Ushito; Hideo Nagasaki; Motoki Yuguchi; Satoshi Yamashita; Masao Tokuda
Journal:  J Am Chem Soc       Date:  2004-11-10       Impact factor: 15.419

7.  Synthetic applications of Pd(II)-catalyzed C-H carboxylation and mechanistic insights: expedient routes to anthranilic acids, oxazolinones, and quinazolinones.

Authors:  Ramesh Giri; Jonathan K Lam; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2010-01-20       Impact factor: 15.419

8.  Rhodium-catalyzed direct oxidative carbonylation of aromatic C-H bond with CO and alcohols.

Authors:  Zheng-Hui Guan; Zhi-Hui Ren; Stephen M Spinella; Shichao Yu; Yong-Min Liang; Xumu Zhang
Journal:  J Am Chem Soc       Date:  2009-01-21       Impact factor: 15.419

9.  Palladium-catalyzed carbonylation reactions of aryl halides and related compounds.

Authors:  Anne Brennführer; Helfried Neumann; Matthias Beller
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Catalytic asymmetric intermolecular Stetter reaction of glyoxamides with alkylidenemalonates.

Authors:  Qin Liu; Stéphane Perreault; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2008-10-04       Impact factor: 15.419
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  33 in total

1.  Pd(II)-catalyzed para-selective C-H arylation of monosubstituted arenes.

Authors:  Xisheng Wang; Dasheng Leow; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-08-16       Impact factor: 15.419

2.  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

3.  Rhodium(III)-catalyzed oxidative carbonylation of benzamides with carbon monoxide.

Authors:  Ya Du; Todd K Hyster; Tomislav Rovis
Journal:  Chem Commun (Camb)       Date:  2011-10-17       Impact factor: 6.222

4.  Ligand-Enabled Arylation of γ-C-H Bonds.

Authors:  Suhua Li; Ru-Yi Zhu; Kai-Jiong Xiao; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2016-02-25       Impact factor: 15.336

5.  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

6.  Aminoquinoline-directed, cobalt-catalyzed carbonylation of sulfonamide sp2 C-H bonds.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Chem Commun (Camb)       Date:  2017-05-04       Impact factor: 6.222

7.  Scope and Mechanistic Study of the Coupling Reaction of α, β-Unsaturated Carbonyl Compounds with Alkenes: Uncovering Electronic Effects on Alkene Insertion vs Oxidative Coupling Pathways.

Authors:  Ki-Hyeok Kwon; Do W Lee; Chae S Yi
Journal:  Organometallics       Date:  2012-01-09       Impact factor: 3.876

Review 8.  Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors:  John C K Chu; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2017-12-05       Impact factor: 15.336

9.  Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes.

Authors:  Masayuki Wasa; Keary M Engle; David W Lin; Eun Jeong Yoo; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2011-11-21       Impact factor: 15.419

10.  Pd(II)-catalyzed C-H iodination using molecular I2 as the sole oxidant.

Authors:  Xiao-Chen Wang; Yi Hu; Samuel Bonacorsi; Yang Hong; Richard Burrell; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2013-07-09       Impact factor: 15.419
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