Literature DB >> 24465074

Mechanistic Studies of Azaphilic versus Carbophilic Activation by Gold(I) in the Gold/Palladium Dual-Catalyzed Rearrangement of Alkenyl Vinyl Aziridines.

Joshua J Hirner1, Katrina E Roth1, Yili Shi1, Suzanne A Blum1.   

Abstract

A vinyl aziridine activation strategy cocatalyzed by palladium(0) and a gold(I) Lewis acid has been developed. This rearrangement installs a C-C and a C-N bond in one synthetic step to form pyrrolizidine and indolizidine products. Two proposed mechanistic roles for the gold cocatalyst were considered: (1) carbophilic gold catalysis or (2) azaphilic gold catalysis. Mechanistic studies support an azaphilic Lewis acid activation of the aziridine over a carbophilic Lewis acid activation of the alkene.

Entities:  

Year:  2012        PMID： 24465074      PMCID： PMC3898857          DOI： 10.1021/om300671j

Source DB:  PubMed          Journal:  Organometallics        ISSN： 0276-7333            Impact factor:   3.876


  58 in total

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Authors:  A Stephen K Hashmi
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Journal:  Chemistry       Date:  2009-10-12       Impact factor: 5.236

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Authors:  Joshua J Hirner; Yili Shi; Suzanne A Blum
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5.  Contemporaneous dual catalysis: chemoselective cross-coupling of catalytic vanadium-allenoate and π-allylpalladium intermediates.

Authors:  Barry M Trost; Xinjun Luan; Yan Miller
Journal:  J Am Chem Soc       Date:  2011-07-22       Impact factor: 15.419

6.  Palladium-catalyzed cross-coupling reactions of organogold(I) reagents with organic electrophiles.

Authors:  Miguel Peña-López; Miguel Ayán-Varela; Luis A Sarandeses; José Pérez Sestelo
Journal:  Chemistry       Date:  2010-08-23       Impact factor: 5.236

7.  Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

Authors:  Daniel A DiRocco; Tomislav Rovis
Journal:  J Am Chem Soc       Date:  2012-05-02       Impact factor: 15.419

8.  Palladium-catalyzed dynamic kinetic asymmetric transformations of vinyl aziridines with nitrogen heterocycles: rapid access to biologically active pyrroles and indoles.

Authors:  Barry M Trost; Maksim Osipov; Guangbin Dong
Journal:  J Am Chem Soc       Date:  2010-11-10       Impact factor: 15.419

9.  Gold(I)-catalyzed intramolecular hydroamination of unactivated C==C bonds with alkyl ammonium salts.

Authors:  Christopher F Bender; Ross A Widenhoefer
Journal:  Chem Commun (Camb)       Date:  2008-05-19       Impact factor: 6.222

10.  Cooperative dual catalysis: application to the highly enantioselective conjugate cyanation of unsaturated imides.

Authors:  Glenn M Sammis; Hiroshi Danjo; Eric N Jacobsen
Journal:  J Am Chem Soc       Date:  2004-08-18       Impact factor: 15.419
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  7 in total

1.  Mechanistic Studies of Gold and Palladium Cooperative Dual-Catalytic Cross-Coupling Systems.

Authors:  Mohammad Al-Amin; Katrina E Roth; Suzanne A Blum
Journal:  ACS Catal       Date:  2014-02-07       Impact factor: 13.084

2.  Gold(I) and Gold(III) Complexes of Cyclic (Alkyl)(amino)carbenes.

Authors:  Alexander S Romanov; Manfred Bochmann
Journal:  Organometallics       Date:  2015-01-29       Impact factor: 3.876

3.  Selectivity, Compatibility, Downstream Functionalization, and Silver Effect in the Gold and Palladium Dual-Catalytic Synthesis of Lactones.

Authors:  Mohammad Al-Amin; Joel S Johnson; Suzanne A Blum
Journal:  Organometallics       Date:  2014-09-09       Impact factor: 3.876

Review 4.  Bimetallic catalysis for C-C and C-X coupling reactions.

Authors:  Dominic R Pye; Neal P Mankad
Journal:  Chem Sci       Date:  2017-01-16       Impact factor: 9.825

5.  Phosphinoindenyl and phosphazidoindenyl complexes of lanthanum and samarium: synthesis, characterisation, and hydroamination catalysis.

Authors:  Matthias R Steiner; Johann A Hlina; Johanna M Uher; Roland C Fischer; Dmytro Neshchadin; Theresa Wilfling
Journal:  Dalton Trans       Date:  2022-02-01       Impact factor: 4.390

6.  Preparation and ring-opening reactions of N-diphenylphosphinyl vinyl aziridines.

Authors:  Ashley N Jarvis; Andrew B McLaren; Helen M I Osborn; Joseph Sweeney
Journal:  Beilstein J Org Chem       Date:  2013-05-02       Impact factor: 2.883

7.  Ring expansion of vinylaziridines through the strain-release pericyclic reaction: recent developments and applications.

Authors:  Yu Mi Heo; Seung-Mann Paek
Journal:  Molecules       Date:  2013-08-12       Impact factor: 4.411
  7 in total

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