Literature DB >> 21894954

Cyanocuprates convert carboxylic acids directly into ketones.

Douglas T Genna1, Gary H Posner.   

Abstract

Carboxylic acids were converted directly in 56-99% yields into methyl, n-butyl, and isopropyl ketones using excess cyanocuprates R(2)CuLi·LiCN. A substrate with a stereocenter α to the carboxylic acid was converted into ketones with very little loss of enantiomeric purity. A variety of functional groups were tolerated including aryl bromides. This direct transformation of a carboxylic acid into ketone with minimal tertiary alcohol formation is proposed to involve a relatively stable copper ketal tetrahedral intermediate.
© 2011 American Chemical Society

Entities:  

Year:  2011        PMID: 21894954     DOI: 10.1021/ol202237j

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

1.  A toxicological study on photo-degradation products of environmental ibuprofen: Ecological and human health implications.

Authors:  Nishanthi Ellepola; Talysa Ogas; Danielle N Turner; Rubi Gurung; Sabino Maldonado-Torres; Rodolfo Tello-Aburto; Praveen L Patidar; Snezna Rogelj; Menake E Piyasena; Gayan Rubasinghege
Journal:  Ecotoxicol Environ Saf       Date:  2019-11-12       Impact factor: 6.291

2.  Design of a novel thiophene inhibitor of 15-lipoxygenase-1 with both anti-inflammatory and neuroprotective properties.

Authors:  Niek G J Leus; Birgit Honrath; Nikolaos Eleftheriadis; Hessel Poelman; Constantinos G Neochoritis; Amalia Dolga; Alexander Dömling; Frank J Dekker
Journal:  Eur J Med Chem       Date:  2016-07-09       Impact factor: 6.514

3.  Conformational Preference of 2'-Fluoro-Substituted Acetophenone Derivatives Revealed by Through-Space 1H-19F and 13C-19F Spin-Spin Couplings.

Authors:  Chinatsu Otake; Takuya Namba; Hidetsugu Tabata; Kosho Makino; Kiriko Hirano; Tetsuta Oshitari; Hideaki Natsugari; Takenori Kusumi; Hideyo Takahashi
Journal:  J Org Chem       Date:  2021-03-01       Impact factor: 4.354

4.  Direct Addition of Grignard Reagents to Aliphatic Carboxylic Acids Enabled by Bulky turbo-Organomagnesium Anilides.

Authors:  Kilian Colas; A Catarina V D Dos Santos; Stefanie V Kohlhepp; Abraham Mendoza
Journal:  Chemistry       Date:  2022-01-27       Impact factor: 5.020

5.  Synthesis of Rumphellaone A and Hushinone by a Gold-Catalyzed [2 + 2] Cycloaddition.

Authors:  Beatrice Ranieri; Carla Obradors; Mauro Mato; Antonio M Echavarren
Journal:  Org Lett       Date:  2016-03-14       Impact factor: 6.005

6.  In Search of Small Molecules That Selectively Inhibit MBOAT4.

Authors:  Emily S Murzinski; Ishika Saha; Hui Ding; David Strugatsky; Ryan A Hollibaugh; Haixia Liu; Peter Tontonoz; Patrick G Harran
Journal:  Molecules       Date:  2021-12-15       Impact factor: 4.411

  6 in total

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