Literature DB >> 21204527

Rhodium(III)-catalyzed arylation of Boc-imines via C-H bond functionalization.

Andy S Tsai1, Michael E Tauchert, Robert G Bergman, Jonathan A Ellman.   

Abstract

The first rhodium-catalyzed arylation of imines proceeding via C-H bond functionalization is reported. Use of a non-coordinating halide abstractor is important to obtain reactivity. Aryl-branched N-Boc-amines are formed, and a wide range of functionality is compatible with the reaction.

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Year:  2011        PMID： 21204527      PMCID： PMC3045530          DOI： 10.1021/ja109562x

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


  27 in total

1.  Rhodium-catalyzed carbon-carbon bond forming reactions of organometallic compounds.

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Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

2.  Oxidative coupling of aromatic substrates with alkynes and alkenes under rhodium catalysis.

Authors:  Tetsuya Satoh; Masahiro Miura
Journal:  Chemistry       Date:  2010-10-04       Impact factor: 5.236

3.  Palladium-catalyzed benzylic addition of 2-methyl azaarenes to N-sulfonyl aldimines via C-H bond activation.

Authors:  Bo Qian; Shengmei Guo; Jianping Shao; Qiming Zhu; Lei Yang; Chungu Xia; Hanmin Huang
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

4.  Stereoselective Pincer-complex catalyzed C-H functionalization of benzyl nitriles under mild conditions. An efficient route to beta-aminonitriles.

Authors:  Juhanes Aydin; Cathrin S Conrad; Kálmán J Szabó
Journal:  Org Lett       Date:  2008-10-28       Impact factor: 6.005

5.  Palladium-catalyzed oxidative alkynylation of alkenes via C-C bond bleavage under oxygen atmosphere.

Authors:  Takahiro Nishimura; Hitoshi Araki; Yasunari Maeda; Sakae Uemura
Journal:  Org Lett       Date:  2003-08-21       Impact factor: 6.005

6.  Ns strategies: a highly versatile synthetic method for amines.

Authors:  Toshiyuki Kan; Tohru Fukuyama
Journal:  Chem Commun (Camb)       Date:  2003-11-25       Impact factor: 6.222

7.  Rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols: synthetic equivalent to asymmetric conjugate alkynylation of enones.

Authors:  Takahiro Nishimura; Taisuke Katoh; Keishi Takatsu; Ryo Shintani; Tamio Hayashi
Journal:  J Am Chem Soc       Date:  2007-10-27       Impact factor: 15.419

8.  Palladium-catalyzed arylation of alpha,alpha-disubstituted arylmethanols via cleavage of a C-C or a C-H bond to give biaryls.

Authors:  Yoshito Terao; Hiroyuki Wakui; Michiyo Nomoto; Tetsuya Satoh; Masahiro Miura; Masakatsu Nomura
Journal:  J Org Chem       Date:  2003-06-27       Impact factor: 4.354

Review 9.  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

10.  Synthesis of aryl ketones by the PD-catalyzed C-H activation of arenes and intermolecular carbopalladation of nitriles.

Authors:  Chengxiang Zhou; Richard C Larock
Journal:  J Am Chem Soc       Date:  2004-03-03       Impact factor: 15.419
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  21 in total

1.  Rhodium catalyzed chelation-assisted C-H bond functionalization reactions.

Authors:  Denise A Colby; Andy S Tsai; Robert G Bergman; Jonathan A Ellman
Journal:  Acc Chem Res       Date:  2011-12-08       Impact factor: 22.384

2.  Rh(III)-Catalyzed C-H Bond Addition/Amine-Mediated Cyclization of Bis-Michael Acceptors.

Authors:  Tyler J Potter; Jonathan A Ellman
Journal:  Org Lett       Date:  2016-07-20       Impact factor: 6.005

Review 3.  Electronic and Steric Tuning of a Prototypical Piano Stool Complex: Rh(III) Catalysis for C-H Functionalization.

Authors:  Tiffany Piou; Tomislav Rovis
Journal:  Acc Chem Res       Date:  2017-12-22       Impact factor: 22.384

4.  Rhodium(iii)-catalyzed synthesis of phthalides by cascade addition and cyclization of benzimidates with aldehydes.

Authors:  Yajing Lian; Robert G Bergman; Jonathan A Ellman
Journal:  Chem Sci       Date:  2012-08-02       Impact factor: 9.825

5.  Cobalt(III)-Catalyzed C-H Bond Amidation with Isocyanates.

Authors:  Joshua R Hummel; Jonathan A Ellman
Journal:  Org Lett       Date:  2015-05-06       Impact factor: 6.005

6.  Rhodium-catalyzed synthesis of branched amines by direct addition of benzamides to imines.

Authors:  Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal:  Org Lett       Date:  2012-04-13       Impact factor: 6.005

7.  Expedient synthesis of N-acyl anthranilamides and β-enamine amides by the Rh(III)-catalyzed amidation of aryl and vinyl C-H bonds with isocyanates.

Authors:  Kevin D Hesp; Robert G Bergman; Jonathan A Ellman
Journal:  J Am Chem Soc       Date:  2011-07-08       Impact factor: 15.419

8.  Transition-Metal-Catalyzed C-H Bond Addition to Carbonyls, Imines, and Related Polarized π Bonds.

Authors:  Joshua R Hummel; Jeffrey A Boerth; Jonathan A Ellman
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

9.  Complementary regioselectivity in Rh(III)-catalyzed insertions of potassium vinyltrifluoroborate via C-H activation: preparation and use of 4-trifluoroboratotetrahydroisoquinolones.

Authors:  Marc Presset; Daniel Oehlrich; Frederik Rombouts; Gary A Molander
Journal:  Org Lett       Date:  2013-03-15       Impact factor: 6.005

10.  Recent Advances in the C-H-Functionalization of the Distal Positions in Pyridines and Quinolines.

Authors:  David E Stephens; Oleg V Larionov
Journal:  Tetrahedron       Date:  2015-08-19       Impact factor: 2.457
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