Literature DB >> 21428310

Cobalt-catalyzed chemoselective insertion of alkene into the ortho C-H bond of benzamide.

Laurean Ilies1, Quan Chen, Xiaoming Zeng, Eiichi Nakamura.   

Abstract

Insertion of 1-alkene, 2-alkene, and styrene into the ortho C-H bond of benzamide in the presence of an inexpensive cobalt catalyst, DMPU as a crucial ligand, and cyclohexylmagnesium chloride proceeds smoothly at 25 °C to selectively give the ortho-alkylated product. Notable features of this reaction include the structural variety of the alkene and the amide substrate and the tolerance of functional groups such as halide, olefin, ester, and amide groups.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID: 21428310     DOI: 10.1021/ja200645w

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


  16 in total

1.  Cobalt-Catalyzed Coupling of Benzoic Acid C-H Bonds with Alkynes, Styrenes, and 1,3-Dienes.

Authors:  Tung Thanh Nguyen; Liene Grigorjeva; Olafs Daugulis
Journal:  Angew Chem Int Ed Engl       Date:  2018-01-10       Impact factor: 15.336

2.  Cobalt-promoted dimerization of aminoquinoline benzamides.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Org Lett       Date:  2015-02-17       Impact factor: 6.005

3.  C2-Alkylation of N-pyrimidylindole with vinylsilane via cobalt-catalyzed C-H bond activation.

Authors:  Zhenhua Ding; Naohiko Yoshikai
Journal:  Beilstein J Org Chem       Date:  2012-09-14       Impact factor: 2.883

4.  Co-catalyzed ortho-C-H functionalization/annulation of arenes and alkenes with alkynylsilanes: access to isoquinolone and pyridone motifs.

Authors:  Cong Lin; Liang Shen
Journal:  RSC Adv       Date:  2019-09-26       Impact factor: 4.036

5.  Cobalt-catalyzed, aminoquinoline-directed coupling of sp(2) C-H bonds with alkenes.

Authors:  Liene Grigorjeva; Olafs Daugulis
Journal:  Org Lett       Date:  2014-08-22       Impact factor: 6.005

Review 6.  Walking Metals for Remote Functionalization.

Authors:  Heiko Sommer; Francisco Juliá-Hernández; Ruben Martin; Ilan Marek
Journal:  ACS Cent Sci       Date:  2018-02-08       Impact factor: 14.553

7.  Copper-catalyzed direct alkylation of heteroarenes.

Authors:  Cédric Theunissen; Jianjun Wang; Gwilherm Evano
Journal:  Chem Sci       Date:  2017-03-20       Impact factor: 9.825

8.  Cobalt(III)-catalyzed synthesis of indazoles and furans by C-H bond functionalization/addition/cyclization cascades.

Authors:  Joshua R Hummel; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2014-12-24       Impact factor: 15.419

9.  Identification of monodentate oxazoline as a ligand for copper-promoted ortho-C-H hydroxylation and amination.

Authors:  Ming Shang; Qian Shao; Shang-Zheng Sun; Yan-Qiao Chen; Hui Xu; Hui-Xiong Dai; Jin-Quan Yu
Journal:  Chem Sci       Date:  2016-09-26       Impact factor: 9.825

10.  Mechanistic insights into cobalt(ii/iii)-catalyzed C-H oxidation: a combined theoretical and experimental study.

Authors:  Xiao-Kang Guo; Lin-Bao Zhang; Donghui Wei; Jun-Long Niu
Journal:  Chem Sci       Date:  2015-09-09       Impact factor: 9.825

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