Literature DB >> 16209612

Practical and efficient Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by recyclable Pd(0)/C.

François-Xavier Felpin1.   

Abstract

The first Suzuki-Miyaura cross-coupling of 2-iodocycloenones with arylboronic acids catalyzed by 10% Pd(0)/C is described as an interesting alternative to classical homogeneous conditions. Most of the substrate reacted under mild condition at 25 degrees C under air in aqueous DME. The conditions described tolerate a wide range of iodoenones and boronic acids. Notably, the procedure features inexpensive reagents and solvents with low toxicity rendering the method environmentally benign. Additionally 10% Pd(0)/C could be recovered and efficiently reused at least five times without significant alteration of the yields of the cross-coupled product.

Entities:  

Year:  2005        PMID: 16209612     DOI: 10.1021/jo051501b

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  15 in total

1.  Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.

Authors:  Micah J Niphakis; Brandon J Turunen; Gunda I Georg
Journal:  J Org Chem       Date:  2010-10-15       Impact factor: 4.354

2.  Enantioselective conjugate allylation of cyclic enones.

Authors:  Douglass F Taber; David A Gerstenhaber; James F Berry
Journal:  J Org Chem       Date:  2011-08-23       Impact factor: 4.354

3.  Direct C-H α-Arylation of Enones with ArI(O2CR)2 Reagents.

Authors:  Felipe Cesar Sousa E Silva; Nguyen T Van; Sarah E Wengryniuk
Journal:  J Am Chem Soc       Date:  2019-12-27       Impact factor: 15.419

4.  Semisynthesis of Platensimycin Derivatives with Antibiotic Activities in Mice via Suzuki-Miyaura Cross-Coupling Reactions.

Authors:  Youchao Deng; Meng Su; Dingding Kang; Xingyun Liu; Zhongqing Wen; Yuling Li; Lin Qiu; Ben Shen; Yanwen Duan; Yong Huang
Journal:  J Med Chem       Date:  2018-12-05       Impact factor: 7.446

5.  Microwave-assisted Suzuki-Miyaura couplings on α-iodoenaminones.

Authors:  Xin Wang; Brandon J Turunen; Matthew W Leighty; Gunda I Georg
Journal:  Tetrahedron Lett       Date:  2007-12-10       Impact factor: 2.415

6.  A three-step route to a tricyclic steroid precursor.

Authors:  Douglass F Taber; Ritesh B Sheth
Journal:  J Org Chem       Date:  2008-09-25       Impact factor: 4.354

7.  Toxicological investigation and antinociceptive property of potassium thiophene-3-trifluoroborate.

Authors:  Roberta A Oliveira; Lucielli Savegnago; Cristiano R Jesse; Paulo H Menezes; Gary A Molander; Cristina W Nogueira
Journal:  Basic Clin Pharmacol Toxicol       Date:  2009-03-27       Impact factor: 4.080

8.  Synthesis and Antiproliferative and Metabolic Evaluations of Novel Securinine Derivatives.

Authors:  Marc Perez; Tahar Ayad; Philippe Maillos; Valérie Poughon; Jacques Fahy; Virginie Ratovelomanana-Vidal
Journal:  ACS Med Chem Lett       Date:  2016-02-02       Impact factor: 4.345

9.  Synthesis and Cytotoxicity of Semisynthetic Withalongolide A Analogues.

Authors:  Hashim F Motiwala; Joseph Bazzill; Abbas Samadi; Huaping Zhang; Barbara N Timmermann; Mark S Cohen; Jeffrey Aubé
Journal:  ACS Med Chem Lett       Date:  2013-11-14       Impact factor: 4.345

10.  Divergent enantioselective synthesis of hapalindole-type alkaloids using catalytic asymmetric hydrogenation of a ketone to construct the chiral core structure.

Authors:  Yang Liu; Li-Jie Cheng; Hai-Tao Yue; Wen Che; Jian-Hua Xie; Qi-Lin Zhou
Journal:  Chem Sci       Date:  2016-04-12       Impact factor: 9.825

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