Literature DB >> 22548244

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

Daniel A DiRocco1, Tomislav Rovis.   

Abstract

Cross-coupling reactions are among the most widely utilized methods for C-C bond formation; however, the requirement of preactivated starting materials still presents a major limitation. Methods that take direct advantage of the inherent reactivity of the C-H bond offer an efficient alternative to these methods, negating the requirement for substrate preactivation. In this process, two chemically distinct activation events culminate in the formation of the desired C-C bond with loss of H(2) as the only byproduct. Herein we report the catalytic asymmetric α-acylation of tertiary amines with aldehydes facilitated by the combination of chiral N-heterocyclic carbene catalysis and photoredox catalysis.

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Year:  2012        PMID: 22548244      PMCID: PMC3354013          DOI: 10.1021/ja3030164

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


  21 in total

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Authors:  Jagan M R Narayanam; Corey R J Stephenson
Journal:  Chem Soc Rev       Date:  2010-06-08       Impact factor: 54.564

2.  Catalytic asymmetric intermolecular Stetter reactions of enolizable aldehydes with nitrostyrenes: computational study provides insight into the success of the catalyst.

Authors:  Daniel A DiRocco; Elizabeth L Noey; K N Houk; Tomislav Rovis
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-26       Impact factor: 15.336

3.  THE PHOTOCHEMISTRY OF THE FUTURE.

Authors:  G Ciamician
Journal:  Science       Date:  1912-09-27       Impact factor: 47.728

4.  Introduction to selective functionalization of C-H bonds.

Authors:  Robert H Crabtree
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

5.  Synthesis of alpha-amido ketones via organic catalysis: thiazolium-catalyzed cross-coupling of aldehydes with acylimines.

Authors:  J A Murry; D E Frantz; A Soheili; R Tillyer; E J Grabowski; P J Reider
Journal:  J Am Chem Soc       Date:  2001-10-03       Impact factor: 15.419

6.  Thiazolium-derived N-heterocyclic carbene-catalyzed cross-coupling of aldehydes with unactivated imines.

Authors:  Gong-Qiang Li; Li-Xin Dai; Shu-Li You
Journal:  Chem Commun (Camb)       Date:  2006-11-23       Impact factor: 6.222

7.  Catalytic additions of acylsilanes to imines: an acyl anion strategy for the direct synthesis of alpha-amino ketones.

Authors:  Anita E Mattson; Karl A Scheidt
Journal:  Org Lett       Date:  2004-11-11       Impact factor: 6.005

8.  Catalytic Synthesis of gamma-Lactams via direct annulations of enals and N-sulfonylimines.

Authors:  Ming He; Jeffrey W Bode
Journal:  Org Lett       Date:  2005-07-07       Impact factor: 6.005

9.  Cross-dehydrogenative coupling (CDC): exploring C-C bond formations beyond functional group transformations.

Authors:  Chao-Jun Li
Journal:  Acc Chem Res       Date:  2009-02-17       Impact factor: 22.384

10.  The catalytic cross-coupling of unactivated arenes.

Authors:  David R Stuart; Keith Fagnou
Journal:  Science       Date:  2007-05-25       Impact factor: 47.728

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  69 in total

1.  Oxazolines as Dual-Function Traceless Chromophores and Chiral Auxiliaries: Enantioselective Photoassisted Synthesis of Polyheterocyclic Ketones.

Authors:  Olga A Mukhina; Andrei G Kutateladze
Journal:  J Am Chem Soc       Date:  2016-02-16       Impact factor: 15.419

2.  Enantioselective conjugate additions of α-amino radicals via cooperative photoredox and Lewis acid catalysis.

Authors:  Laura Ruiz Espelt; Iain S McPherson; Eric M Wiensch; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2015-02-16       Impact factor: 15.419

3.  Enantioselective Excited-State Photoreactions Controlled by a Chiral Hydrogen-Bonding Iridium Sensitizer.

Authors:  Kazimer L Skubi; Jesse B Kidd; Hoimin Jung; Ilia A Guzei; Mu-Hyun Baik; Tehshik P Yoon
Journal:  J Am Chem Soc       Date:  2017-11-16       Impact factor: 15.419

4.  Photocatalytic Oxyamination of Alkenes: Copper(II) Salts as Terminal Oxidants in Photoredox Catalysis.

Authors:  Nicholas L Reed; Madeline I Herman; Vladimir P Miltchev; Tehshik P Yoon
Journal:  Org Lett       Date:  2018-11-08       Impact factor: 6.005

5.  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

6.  Asymmetric photoredox transition-metal catalysis activated by visible light.

Authors:  Haohua Huo; Xiaodong Shen; Chuanyong Wang; Lilu Zhang; Philipp Röse; Liang-An Chen; Klaus Harms; Michael Marsch; Gerhard Hilt; Eric Meggers
Journal:  Nature       Date:  2014-11-06       Impact factor: 49.962

7.  Catalysis: dual catalysis at the flick of a switch.

Authors:  James J Devery; Corey R J Stephenson
Journal:  Nature       Date:  2015-03-05       Impact factor: 49.962

8.  Visible-light sensitization of vinyl azides by transition-metal photocatalysis.

Authors:  Elliot P Farney; Tehshik P Yoon
Journal:  Angew Chem Int Ed Engl       Date:  2013-11-26       Impact factor: 15.336

9.  Transition metal photoredox catalysis of radical thiol-ene reactions.

Authors:  Elizabeth L Tyson; Michael S Ament; Tehshik P Yoon
Journal:  J Org Chem       Date:  2012-11-12       Impact factor: 4.354

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

Authors:  Joshua J Hirner; Katrina E Roth; Yili Shi; Suzanne A Blum
Journal:  Organometallics       Date:  2012-10-08       Impact factor: 3.876

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