Manganese-Catalyzed Carboacylations of Alkenes with Alkyl Iodides
- PMID: 27505233
- PMCID: PMC5359471
- DOI: 10.1021/acs.orglett.6b02154
Manganese-Catalyzed Carboacylations of Alkenes with Alkyl Iodides
Abstract
A manganese-catalyzed carboacylation of alkenes with alkyl iodides and carbon monoxide is described. This carbonylative difunctionalization uses both primary and secondary alkyl iodides in reactions with a diverse array of cyclic and acyclic substrates. Examples of successful applications to the synthesis of five-, six-, and seven-membered rings are provided. The inexpensive, first-row catalytic system and mild reaction conditions are expected to facilitate applications in complex synthesis.
Figures
References
-
- Gu J, Wang X, Xue W, Gong H. Org Chem Front. 2015;2:1411.
- Iwasaki T, Kambe N. In: Comprehensive Organic Synthesis II. Knochel P, Molander GA, editors. Vol. 3. Elsevier; Amsterdam: 2014. pp. 337–391.
- Hu X. Chem Sci. 2011;2
- Kambe N, Iwasaki T, Terao J. Chem Soc Rev. 2011;40:4937. - PubMed
- Rudolph A, Lautens M. Angew Chem Int Ed. 2009;48:2656. - PubMed
- Frisch AC, Beller M. Angew Chem Int Ed. 2005;44:674. - PubMed
-
- Lebedev SA, Lopatina VS, Petrov ES, Beletskaya IPJ. Organomet Chem. 1988;344:253.
- Terao J, Watabe H, Miyamoto M, Kambe N. Bull Chem Soc Jpn. 2003;76:2209.
- Affo W, Ohmiya H, Fujioka T, Ikeda Y, Nakamura T, Yorimitsu H, Oshima K, Imamura Y, Mizuta T, Miyoshi K. J Am Chem Soc. 2006;128:8068. - PubMed
- Firmansjah L, Fu GCJ. Am Chem Soc. 2007;129:11340. - PubMed
- Bloome KS, McMahen RL, Alexanian EJ. J Am Chem Soc. 2011;133:20146. - PubMed
- Weiss ME, Kreis LM, Lauber A, Carreira EM. Angew Chem Int Ed. 2011;50:11125. - PubMed
- Millán A, Álvarez de Cienfuegos L, Miguel D, Campaña AG, Cuerva JM. Org Lett. 2012;14:5984. - PubMed
- McMahon CM, Alexanian EJ. Angew Chem Int Ed. 2014;53:5974. - PubMed
- Zou Y, Zhou J. Chem Commun. 2014;50:3725. - PubMed
- Yang F, Fu SY, Chu W, Li C, Tong DG. RSC Adv. 2014;4:45838.
- Ilves L, Matsubara T, Ichikawa S, Asako S, Nakamura EJ. Am Chem Soc. 2014;36:13126. - PubMed
- Parasaram M, Iaroshenko VO, Gevorgyan V. J Am Chem Soc. 2014;136:17926. - PMC - PubMed
- Fu SY, Li YZ, Chu W, Li C, Tong DG. Catal Sci Technol. 2015;5:1638.
- Liu W, Lu L, Zhengwang C, Li C. Org Biomol Chem. 2015;13:6170. - PubMed
-
-
For a photochemical palladium-catalyzed carboacylation using activated alkyl halides and high CO pressure (45 atm), see:
- Fusano A, Sumino S, Fukuyama T, Ryu I. Org Lett. 2011;13:2114. - PubMed
-
For aryl carboacylations see:
- Seashore-Ludlow B, Danielsson J, Somfai P. Adv Synth Catal. 2012;354:205.
- Liu C, Widenhoefer RA. J Am Chem Soc. 2004;126:10250. - PubMed
-
-
- Ishiyama T, Murata M, Suzuki A, Miyaura N. J Chem Soc, Chem Commun. 1995:295.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
