Literature DB >> 17877360

Direct carbon-carbon bond formation via soft enolization: a facile and efficient synthesis of 1,3-diketones.

Daniel Lim1, Fang Fang, Guoqiang Zhou, Don M Coltart.   

Abstract

Ketones undergo soft enolate formation and acylation on treatment with MgBr(2).OEt(2), i-Pr(2)NEt, and various acylating agents to give 1,3-diketones. The process is particularly efficient for N-acylbenzotriazoles and O-Pfp esters, and, in these cases, is conducted with untreated, reagent-grade CH(2)Cl(2) open to the air, thus providing an exceptionally simple approach to the synthesis of this important class of compounds.

Entities:  

Year:  2007        PMID: 17877360     DOI: 10.1021/ol701599v

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


  7 in total

1.  Bond-weakening catalysis: conjugate aminations enabled by the soft homolysis of strong N-H bonds.

Authors:  Kyle T Tarantino; David C Miller; Ted A Callon; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2015-05-13       Impact factor: 15.419

2.  Efficient Synthesis of 6,6´-Diamido-2,2´-dipicolylamine Ligands for Potential Phosphate Anion Sensing.

Authors:  Shuai Wang; Lichong Gong; Georges El Fakhri; Junfeng Wang
Journal:  New J Chem       Date:  2021-08-17       Impact factor: 3.925

3.  (CF3CO)2O/CF3SO3H-mediated synthesis of 1,3-diketones from carboxylic acids and aromatic ketones.

Authors:  JungKeun Kim; Elvira Shokova; Victor Tafeenko; Vladimir Kovalev
Journal:  Beilstein J Org Chem       Date:  2014-09-26       Impact factor: 2.883

4.  Synthesis and crystal structure of methyl 3-(3-hy-droxy-3-phenyl-prop-2-eno-yl)benzoate.

Authors:  Irina S Zharinova; Alfiya A Bilyalova; Stanislav I Bezzubov
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2018-05-18

5.  Observation of 1,3-diketones formation in the reaction of bulky acyl chlorides with methyllithium.

Authors:  Jian Zhang; Nianfa Yang; Liwen Yang
Journal:  Molecules       Date:  2012-05-29       Impact factor: 4.411

6.  Silicon Industry Waste Polymethylhydrosiloxane-Mediated Benzotriazole Ring Cleavage: A Practical and Green Synthesis of Diverse Benzothiazoles.

Authors:  Mangal S Yadav; Anoop S Singh; Anand K Agrahari; Nidhi Mishra; Vinod K Tiwari
Journal:  ACS Omega       Date:  2019-04-11

7.  Dual Glycolate Oxidase/Lactate Dehydrogenase A Inhibitors for Primary Hyperoxaluria.

Authors:  Jinyue Ding; Rajesh Gumpena; Marc-Olivier Boily; Alexandre Caron; Oliver Chong; Jennifer H Cox; Valerie Dumais; Samuel Gaudreault; Aaron H Graff; Andrew King; John Knight; Renata Oballa; Jayakumar Surendradoss; Tim Tang; Joyce Wu; W Todd Lowther; David A Powell
Journal:  ACS Med Chem Lett       Date:  2021-05-20       Impact factor: 4.632

  7 in total

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