Literature DB >> 30693768

Rhodium-Catalyzed Aldehyde Arylation via Formate-Mediated Transfer Hydrogenation: Beyond Metallic Reductants in Grignard/Nozaki-Hiyami-Kishi-Type Addition.

Robert A Swyka1, Wandi Zhang1, Jeffery Richardson2, J Craig Ruble3, Michael J Krische1.   

Abstract

The first intermolecular carbonyl arylations via transfer hydrogenative reductive coupling are described. Using rhodium catalysts modified by tBu2PMe, sodium formate-mediated reductive coupling of aryl iodides with aldehydes occurs in a chemoselective fashion in the presence of protic functional groups and lower halides. This work expands the emerging paradigm of transfer hydrogenative coupling as an alternative to pre-formed carbanions or metallic reductants in C═X addition.

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Year:  2019        PMID： 30693768      PMCID： PMC6376962          DOI： 10.1021/jacs.8b13652

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


  42 in total

1.  Catalytic enantioselective addition to imines.

Authors:  S Kobayashi; H Ishitani
Journal:  Chem Rev       Date:  1999-05-12       Impact factor: 60.622

2.  Carbonminus signCarbon Bond Formations Involving Organochromium(III) Reagents.

Authors:  Alois Fürstner
Journal:  Chem Rev       Date:  1999-04-14       Impact factor: 60.622

3.  Metal-mediated reductive hydrodehalogenation of organic halides.

Authors:  Francisco Alonso; Irina P Beletskaya; Miguel Yus
Journal:  Chem Rev       Date:  2002-11       Impact factor: 60.622

4.  Ni(II)/Zn-Mediated chemoselective arylation of aromatic aldehydes: facile synthesis of diaryl carbinols

Authors: 
Journal:  Org Lett       Date:  2000-07-27       Impact factor: 6.005

Review 5.  Catalytic asymmetric organozinc additions to carbonyl compounds.

Authors:  L Pu; H B Yu
Journal:  Chem Rev       Date:  2001-03       Impact factor: 60.622

6.  An electrochemical coupling of organic halide with aldehydes, catalytic in chromium and nickel salts. the Nozaki-Hiyama-Kishi reaction.

Authors:  M Durandetti; J Y Nédélec; J Périchon
Journal:  Org Lett       Date:  2001-06-28       Impact factor: 6.005

7.  Direct observation of aldehyde insertion into rhodium-aryl and -alkoxide complexes.

Authors:  Christopher Krug; John F Hartwig
Journal:  J Am Chem Soc       Date:  2002-02-27       Impact factor: 15.419

8.  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

Review 9.  Nickel-catalyzed reductive cyclizations and couplings.

Authors:  John Montgomery
Journal:  Angew Chem Int Ed Engl       Date:  2004-07-26       Impact factor: 15.336

10.  Synthesis of phthalide derivatives using nickel-catalyzed cyclization of o-haloesters with aldehydes.

Authors:  Dinesh Kumar Rayabarapu; Hong-Tai Chang; Chien-Hong Cheng
Journal:  Chemistry       Date:  2004-06-21       Impact factor: 5.236
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  5 in total

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

Authors:  William G Shuler; Robert A Swyka; Tabitha T Schempp; Brian J Spinello; Michael J Krische
Journal:  Chemistry       Date:  2019-09-04       Impact factor: 5.236

2.  Conversion of Aldehydes to Branched or Linear Ketones via Regiodivergent Rhodium-Catalyzed Vinyl Bromide Reductive Coupling-Redox Isomerization Mediated by Formate.

Authors:  Robert A Swyka; William G Shuler; Brian J Spinello; Wandi Zhang; Chunling Lan; Michael J Krische
Journal:  J Am Chem Soc       Date:  2019-04-18       Impact factor: 15.419

3.  Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes To Form Hindered Secondary Alcohols.

Authors:  Kevin J Garcia; Michael M Gilbert; Daniel J Weix
Journal:  J Am Chem Soc       Date:  2019-01-29       Impact factor: 15.419

4.  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

5.  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
  5 in total

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