Literature DB >> 31403727

Vinyl Triflate-Aldehyde Reductive Coupling-Redox Isomerization Mediated by Formate: Rhodium-Catalyzed Ketone Synthesis in the Absence of Stoichiometric Metals.

William G Shuler1, Robert A Swyka1, Tabitha T Schempp1, Brian J Spinello1, Michael J Krische1.   

Abstract

Direct conversion of aldehydes to ketones is achieved via rhodium-catalyzed vinyl triflate-aldehyde reductive coupling-redox isomerization mediated by potassium formate. This method circumvents premetalated C-nucleophiles and discrete redox manipulations typically required to form ketones from aldehydes.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  C−C bond formation; formate; redox isomerization; rhodium; transfer hydrogenation

Year:  2019        PMID： 31403727      PMCID： PMC6763374          DOI： 10.1002/chem.201903668

Source DB:  PubMed          Journal:  Chemistry        ISSN： 0947-6539            Impact factor:   5.236


  40 in total

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Authors:  Ramalinga Uma; Christophe Crévisy; René Grée
Journal:  Chem Rev       Date:  2003-01       Impact factor: 60.622

2.  Hydrogen-mediated C-C bond formation: a broad new concept in catalytic C-C coupling.

Authors:  Ming-Yu Ngai; Jong-Rock Kong; Michael J Krische
Journal:  J Org Chem       Date:  2007-02-16       Impact factor: 4.354

3.  Synthesis of the lycopodium alkaloid (+)-lycoflexine.

Authors:  Jürgen Ramharter; Harald Weinstabl; Johann Mulzer
Journal:  J Am Chem Soc       Date:  2010-10-20       Impact factor: 15.419

4.  Hydroacylation of 2-Butyne from the Alcohol or Aldehyde Oxidation Level via Ruthenium Catalyzed C-C Bond Forming Transfer Hydrogenation.

Authors:  Vanessa M Williams; Joyce C Leung; Ryan L Patman; Michael J Krische
Journal:  Tetrahedron       Date:  2009-06-27       Impact factor: 2.457

5.  Palladium-catalyzed synthesis of aryl ketones by coupling of aryl bromides with an acyl anion equivalent.

Authors:  Akihiro Takemiya; John F Hartwig
Journal:  J Am Chem Soc       Date:  2006-11-22       Impact factor: 15.419

6.  Nickel-catalyzed coupling of aryl iodides with aromatic aldehydes: chemoselective synthesis of ketones.

Authors:  Yi-Chun Huang; Kanak Kanti Majumdar; Chien-Hong Cheng
Journal:  J Org Chem       Date:  2002-03-08       Impact factor: 4.354

7.  Cooperative catalysis by ru and pd for the direct coupling of a chelating aldehyde with iodoarenes or organostannanes.

Authors:  Sangwon Ko; Byungman Kang; Sukbok Chang
Journal:  Angew Chem Int Ed Engl       Date:  2005-01-07       Impact factor: 15.336

8.  Diene hydroacylation from the alcohol or aldehyde oxidation level via ruthenium-catalyzed C-C bond-forming transfer hydrogenation: synthesis of beta,gamma-unsaturated ketones.

Authors:  Fumitoshi Shibahara; John F Bower; Michael J Krische
Journal:  J Am Chem Soc       Date:  2008-10-08       Impact factor: 15.419

9.  Convenient processes for the synthesis of aromatic ketones from aryl bromides and carboxylic anhydrides using a cobalt catalysis.

Authors:  Igor Kazmierski; Mylène Bastienne; Corinne Gosmini; Jean-Marc Paris; Jacques Périchon
Journal:  J Org Chem       Date:  2004-02-06       Impact factor: 4.354

10.  Direct acylation of aryl bromides with aldehydes by palladium catalysis.

Authors:  Jiwu Ruan; Ourida Saidi; Jonathan A Iggo; Jianliang Xiao
Journal:  J Am Chem Soc       Date:  2008-07-18       Impact factor: 15.419
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  3 in total

1.  Conversion of Primary Alcohols and Butadiene to Branched Ketones via Merged Transfer Hydrogenative Carbonyl Addition-Redox Isomerization Catalyzed by Rhodium.

Authors:  Brian J Spinello; Jessica Wu; Yoon Cho; Michael J Krische
Journal:  J Am Chem Soc       Date:  2021-08-20       Impact factor: 16.383

2.  Formate-Mediated Cross-Electrophile Reductive Coupling of Aryl Iodides and Bromopyridines.

Authors:  Leyah A Schwartz; Kim Spielmann; Robert A Swyka; Ming Xiang; Michael J Krische
Journal:  Isr J Chem       Date:  2020-10-15       Impact factor: 3.333

3.  From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.

Authors:  Catherine Gazolla Santana; Michael J Krische
Journal:  ACS Catal       Date:  2021-04-22       Impact factor: 13.084
  3 in total

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