Literature DB >> 23919250

Pd(0)-catalyzed sequential C-N bond formation via allylic and aromatic C-H amination of α-methylstyrenes with diaziridinone.

Thomas A Ramirez1, Qian Wang, Yingguang Zhu, Huaiji Zheng, Xingao Peng, Richard G Cornwall, Yian Shi.   

Abstract

A novel Pd(0)-catalyzed sequential C-N bond formation process via allylic and aromatic C-H amination of α-methylstyrenes with di-tert-butyldiaziridinone, giving spirocyclic indolines in good yields, is described. Four C-N bonds and one spiro quaternary carbon are generated in a single operation.

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Year:  2013        PMID： 23919250      PMCID： PMC3864675          DOI： 10.1021/ol401935c

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  66 in total

1.  Metal-Initiated Amination of Alkenes and Alkynes.

Authors:  Thomas E. Müller; Matthias Beller
Journal:  Chem Rev       Date:  1998-04-02       Impact factor: 60.622

2.  Enantioselective catalytic aziridinations and asymmetric nitrene insertions into CH bonds.

Authors:  Paul Müller; Corinne Fruit
Journal:  Chem Rev       Date:  2003-08       Impact factor: 60.622

3.  Recent advances in catalytic intramolecular C-H aminations.

Authors:  Huw M L Davies; Matthew S Long
Journal:  Angew Chem Int Ed Engl       Date:  2005-06-06       Impact factor: 15.336

4.  Palladium(II)-Catalyzed Cyclization of Olefinic Tosylamides.

Authors:  Richard C. Larock; Timothy R. Hightower; Lisa A. Hasvold; Karl P. Peterson
Journal:  J Org Chem       Date:  1996-05-31       Impact factor: 4.354

5.  Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

Authors:  Hung-Yat Thu; Wing-Yiu Yu; Chi-Ming Che
Journal:  J Am Chem Soc       Date:  2006-07-19       Impact factor: 15.419

6.  Synthesis and insertion reactions of the cyclometalated palladium-alkyl complexes Pd(CH(2)CMe(2)-o-C(6)H(4))L(2). Observation of a pentacoordinated intermediate in the insertion of SO(2).

Authors:  J Cámpora; J A López; P Palma; D del Rio; E Carmona; P Valerga; C Graiff; A Tiripicchio
Journal:  Inorg Chem       Date:  2001-08-13       Impact factor: 5.165

7.  The renaissance of palladium(II)-catalyzed oxidation chemistry.

Authors:  Matthew S Sigman; Mitchell J Schultz
Journal:  Org Biomol Chem       Date:  2004-08-23       Impact factor: 3.876

Review 8.  Vicinal diamino functionalities as privileged structural elements in biologically active compounds and exploitation of their synthetic chemistry.

Authors:  S R S Saibabu Kotti; Cody Timmons; Guigen Li
Journal:  Chem Biol Drug Des       Date:  2006-02       Impact factor: 2.817

9.  Asymmetric allylic alkylation, an enabling methodology.

Authors:  Barry M Trost
Journal:  J Org Chem       Date:  2004-09-03       Impact factor: 4.354

10.  Modern synthetic methods for copper-mediated C(aryl)[bond]O, C(aryl)[bond]N, and C(aryl)[bond]S bond formation.

Authors:  Steven V Ley; Andrew W Thomas
Journal:  Angew Chem Int Ed Engl       Date:  2003-11-17       Impact factor: 15.336
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  4 in total

Review 1.  Cross-Coupling of Heteroatomic Electrophiles.

Authors:  Katerina M Korch; Donald A Watson
Journal:  Chem Rev       Date:  2019-06-11       Impact factor: 60.622

2.  Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C─H activation.

Authors:  Alexander J Rago; Guangbin Dong
Journal:  Green Synth Catal       Date:  2021-03-04

3.  Palladium(0)-catalyzed Heck reaction/C-H activation/amination sequence with diaziridinone: a facile approach to indolines.

Authors:  Huaiji Zheng; Yingguang Zhu; Yian Shi
Journal:  Angew Chem Int Ed Engl       Date:  2014-09-04       Impact factor: 15.336

4.  Catalytic diamination of olefins via N-N bond activation.

Authors:  Yingguang Zhu; Richard G Cornwall; Haifeng Du; Baoguo Zhao; Yian Shi
Journal:  Acc Chem Res       Date:  2014-11-17       Impact factor: 22.384
  4 in total

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