Literature DB >> 26912852

Asymmetric copper-catalyzed C-N cross-couplings induced by visible light.

Quirin M Kainz1, Carson D Matier1, Agnieszka Bartoszewicz1, Susan L Zultanski1, Jonas C Peters1, Gregory C Fu1.   

Abstract

Despite a well-developed and growing body of work in copper catalysis, the potential of copper to serve as a photocatalyst remains underexplored. Here we describe a photoinduced copper-catalyzed method for coupling readily available racemic tertiary alkyl chloride electrophiles with amines to generate fully substituted stereocenters with high enantioselectivity. The reaction proceeds at -40°C under excitation by a blue light-emitting diode and benefits from the use of a single, Earth-abundant transition metal acting as both the photocatalyst and the source of asymmetric induction. An enantioconvergent mechanism transforms the racemic starting material into a single product enantiomer.
Copyright © 2016, American Association for the Advancement of Science.

Entities:  

Year:  2016        PMID: 26912852      PMCID: PMC4770572          DOI: 10.1126/science.aad8313

Source DB:  PubMed          Journal:  Science        ISSN: 0036-8075            Impact factor:   47.728


  24 in total

1.  Catalytic enantioselective reactions driven by photoinduced electron transfer.

Authors:  Andreas Bauer; Felix Westkämper; Stefan Grimme; Thorsten Bach
Journal:  Nature       Date:  2005-08-25       Impact factor: 49.962

Review 2.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal:  Chem Rev       Date:  2013-03-19       Impact factor: 60.622

3.  Use of a new spirophosphine to achieve catalytic enantioselective [4 + 1] annulations of amines with allenes to generate dihydropyrroles.

Authors:  Søren Kramer; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2015-03-17       Impact factor: 15.419

4.  Photoinduced, copper-catalyzed alkylation of amides with unactivated secondary alkyl halides at room temperature.

Authors:  Hien-Quang Do; Shoshana Bachman; Alex C Bissember; Jonas C Peters; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2014-01-21       Impact factor: 15.419

5.  Stereoconvergent amine-directed alkyl-alkyl Suzuki reactions of unactivated secondary alkyl chlorides.

Authors:  Zhe Lu; Ashraf Wilsily; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2011-05-10       Impact factor: 15.419

6.  Catalytic enantioselective synthesis of quaternary carbon stereocentres.

Authors:  Kyle W Quasdorf; Larry E Overman
Journal:  Nature       Date:  2014-12-11       Impact factor: 49.962

7.  Asymmetric Suzuki cross-couplings of activated secondary alkyl electrophiles: arylations of racemic alpha-chloroamides.

Authors:  Pamela M Lundin; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2010-08-18       Impact factor: 15.419

8.  Total syntheses of murrayamine E, I, and K.

Authors:  Christian Schuster; Konstanze K Julich-Gruner; Heinrich Schnitzler; Ronny Hesse; Anne Jäger; Arndt W Schmidt; Hans-Joachim Knölker
Journal:  J Org Chem       Date:  2015-05-12       Impact factor: 4.354

Review 9.  Solar synthesis: prospects in visible light photocatalysis.

Authors:  Danielle M Schultz; Tehshik P Yoon
Journal:  Science       Date:  2014-02-28       Impact factor: 47.728

10.  Iron-Catalyzed Enantioselective Cross-Coupling Reactions of α-Chloroesters with Aryl Grignard Reagents.

Authors:  Masayoshi Jin; Laksmikanta Adak; Masaharu Nakamura
Journal:  J Am Chem Soc       Date:  2015-05-22       Impact factor: 15.419

View more
  91 in total

1.  An enzymatic platform for the asymmetric amination of primary, secondary and tertiary C(sp3)-H bonds.

Authors:  Yang Yang; Inha Cho; Xiaotian Qi; Peng Liu; Frances H Arnold
Journal:  Nat Chem       Date:  2019-10-14       Impact factor: 24.427

2.  Copper-Catalyzed Alkylation of Aliphatic Amines Induced by Visible Light.

Authors:  Carson D Matier; Jonas Schwaben; Jonas C Peters; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2017-11-28       Impact factor: 15.419

3.  Activation of C-O and C-N Bonds Using Non-Precious-Metal Catalysis.

Authors:  Timothy B Boit; Ana S Bulger; Jacob E Dander; Neil K Garg
Journal:  ACS Catal       Date:  2020-09-10       Impact factor: 13.084

Review 4.  Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/O2 Model Systems to Organometallic Transformations.

Authors:  Rachel Trammell; Khashayar Rajabimoghadam; Isaac Garcia-Bosch
Journal:  Chem Rev       Date:  2019-01-30       Impact factor: 60.622

5.  Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis.

Authors:  Taehoon Kim; Stefan J McCarver; Chulbom Lee; David W C MacMillan
Journal:  Angew Chem Int Ed Engl       Date:  2018-02-27       Impact factor: 15.336

Review 6.  The Fascinating Chemistry of α-Haloamides.

Authors:  Anna Fantinati; Vinicio Zanirato; Paolo Marchetti; Claudio Trapella
Journal:  ChemistryOpen       Date:  2020-01-13       Impact factor: 2.911

7.  Design of a Photoredox Catalyst that Enables the Direct Synthesis of Carbamate-Protected Primary Amines via Photoinduced, Copper-Catalyzed N-Alkylation Reactions of Unactivated Secondary Halides.

Authors:  Jun Myun Ahn; Jonas C Peters; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2017-12-04       Impact factor: 15.419

8.  Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Acyclic α-N-Pyrrolyl/Indolyl Ketones.

Authors:  Remi Lavernhe; Eric J Alexy; Haiming Zhang; Brian M Stoltz
Journal:  Org Lett       Date:  2020-05-18       Impact factor: 6.005

9.  Photoinduced, Copper-Catalyzed Decarboxylative C-N Coupling to Generate Protected Amines: An Alternative to the Curtius Rearrangement.

Authors:  Wei Zhao; Ryan P Wurz; Jonas C Peters; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2017-08-25       Impact factor: 15.419

10.  Structure-Property Relationships for Tailoring Phenoxazines as Reducing Photoredox Catalysts.

Authors:  Blaine G McCarthy; Ryan M Pearson; Chern-Hooi Lim; Steven M Sartor; Niels H Damrauer; Garret M Miyake
Journal:  J Am Chem Soc       Date:  2018-03-27       Impact factor: 15.419

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.