1,4-Diiodo-1,3-dienes: versatile reagents in organic synthesis
- PMID: 20853391
- DOI: 10.1002/asia.201000405
1,4-Diiodo-1,3-dienes: versatile reagents in organic synthesis
Abstract
1,4-Diiodo-1,3-dienes are unique reagents in organic synthesis and have been employed in several well-known and recently developed areas of application. Furthermore, these dienes are easily accessible, starting from the alkynes and iodine, and they have demonstrated high reactivity in cross-coupling reactions, organometallic synthesis, in the preparation of heterocyclic compounds, and several other transformations. The high reactivity of the 1,4-diiodo-1,3-dienes allows for the development of synthetic procedures that use mild conditions (room temperature). The key advantages in assembling complex organic molecules, natural products, and compounds for material science using 1,4-diiodo-1,3-dienes as building blocks include high yields, excellent selectivity, and diverse reactivity in carbon-carbon and carbon-heteroatom bond formation. This Focus Review describes the scope and application of the 1,4-diiodo-1,3-dienes in organic synthesis as well as summarizes the methods for preparation of the dienes.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
Stereoselective synthesis of trisubstituted (E,E)-1,3-dienes by the site-selective reductive cross-coupling of internal alkynes with terminal alkynes: a fragment coupling reaction for natural product synthesis.J Org Chem. 2009 Oct 2;74(19):7211-9. doi: 10.1021/jo901451c. J Org Chem. 2009. PMID: 19722544
-
Cross-coupling reaction of alkyl halides with grignard reagents catalyzed by Ni, Pd, or Cu complexes with pi-carbon ligand(s).Acc Chem Res. 2008 Nov 18;41(11):1545-54. doi: 10.1021/ar800138a. Acc Chem Res. 2008. PMID: 18973349
-
Alkoxyallenes as building blocks for organic synthesis.Chem Soc Rev. 2014 May 7;43(9):2888-903. doi: 10.1039/c3cs60429b. Epub 2014 Feb 19. Chem Soc Rev. 2014. PMID: 24549322 Review.
-
1,4-Dilithio-1,3-dienes: reaction and synthetic applications.Acc Chem Res. 2010 Oct 19;43(10):1342-51. doi: 10.1021/ar1000583. Acc Chem Res. 2010. PMID: 20954749
-
Conjugate addition reactions of carbon nucleophiles to electron-deficient dienes.Chem Soc Rev. 2010 Nov;39(11):4080-102. doi: 10.1039/b924486g. Epub 2010 Jul 29. Chem Soc Rev. 2010. PMID: 20668736 Review.
Cited by
-
Taming Highly Unstable Radical Anions and 1,4-Organodilithiums by Flow Microreactors: Controlled Reductive Dimerization of Styrenes.JACS Au. 2022 Oct 31;2(11):2514-2521. doi: 10.1021/jacsau.2c00375. eCollection 2022 Nov 28. JACS Au. 2022. PMID: 36465543 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources