Literature DB >> 30998328

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

Robert A Swyka1, William G Shuler1, Brian J Spinello1, Wandi Zhang1, Chunling Lan1, Michael J Krische1.   

Abstract

A regiodivergent catalytic method for direct conversion of aldehydes to branched or linear alkyl ketones is described. Rhodium complexes modified by P tBu2Me catalyze formate-mediated aldehyde-vinyl bromide reductive coupling-redox isomerization to form branched ketones. Use of the less strongly coordinating ligand, PPh3, promotes vinyl- to allylrhodium isomerization en route to linear ketones. This method bypasses the 3-step sequence often used to convert aldehydes to ketones involving the addition of pre-metalated reagents to Weinreb or morpholine amides.

Entities:  

Year:  2019        PMID： 30998328      PMCID： PMC6602061          DOI： 10.1021/jacs.9b03113

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


  30 in total

1.  Transposition of allylic alcohols into carbonyl compounds mediated by transition metal complexes.

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

2.  Reactivity of the latent 12-electron fragment [Rh(PiBu3)2]+ with aryl bromides: aryl-Br and phosphine ligand C-H activation.

Authors:  Nell S Townsend; Adrian B Chaplin; M Abu Naser; Amber L Thompson; Nicholas H Rees; Stuart A Macgregor; Andrew S Weller
Journal:  Chemistry       Date:  2010-07-26       Impact factor: 5.236

3.  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

4.  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

5.  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

6.  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

7.  Negishi coupling of secondary alkylzinc halides with aryl bromides and chlorides.

Authors:  Chong Han; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2009-06-10       Impact factor: 15.419

8.  Chelation-assisted carbon-halogen bond activation by a rhodium(I) complex.

Authors:  Shanshan Chen; Yongxin Li; Jing Zhao; Xingwei Li
Journal:  Inorg Chem       Date:  2009-02-02       Impact factor: 5.165

9.  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

10.  Direct observation of beta-aryl eliminations from Rh(I) alkoxides.

Authors:  Pinjing Zhao; Christopher D Incarvito; John F Hartwig
Journal:  J Am Chem Soc       Date:  2006-03-15       Impact factor: 15.419
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  4 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 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

3.  Intermolecular diastereoselective annulation of azaarenes into fused N-heterocycles by Ru(II) reductive catalysis.

Authors:  He Zhao; Yang Wu; Chenggang Ci; Zhenda Tan; Jian Yang; Huanfeng Jiang; Pierre H Dixneuf; Min Zhang
Journal:  Nat Commun       Date:  2022-05-02       Impact factor: 17.694

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
  4 in total

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