Metallophytes for organic synthesis: towards new bio-based selective protection/deprotection procedures
- 1.1k Downloads
We propose for the first time using metal hyperaccumulating plants for the construction of a repertoire of protection and deprotection conditions in a concept of orthogonal sets. Protection of alcohol, carbonyl, carboxyl, and amino groups are considered. The ecocatalysts derived from metal-rich plants allow selective, mild, eco-friendly, and efficient protection or deprotection reactions. The selectivity is controlled by the choice of the metal, which is hyperaccumulated by the metallophyte.
KeywordsEcocatalysis Bio-based chemistry Protecting groups Metal hyperaccumulating plants Phytoextraction
The authors would like to thank the Agence Nationale de la Recherche (ANR 11ECOT 011 01), Centre National de la Recherche Scientifique (CNRS), Agence de l’Environnement et de la Maîtrise de l’Energie (ADEME), and Fond Européen de Développement Régional (FEDER) program for their financial supports.
- Bao K. Zhang W. Bu X. Song Z. Zhang L. Cheng M. (2008). A novel type of N-formylation and related reactions of amines via cyanides and esters as formylating agents. Chem Commun 5429–5431Google Scholar
- Greene TW, Wuts PGM (1991) Protective groups in organic synthesis. Wiley, New YorkGoogle Scholar
- Grison C. Escande V (2012). Use of certain manganese-accumulating plants for carrying out organic chemistry reactions. WO 2014/016509 A1.Google Scholar
- Grison C. Escande V (2013). Use of certain metal-accumulating plants for implementing organic chemistry reactions. WO 2013150197 A1Google Scholar
- Grison C. Escande V. (2014). Use of particular metal accumulating plants for implementing catalyzed chemical reactions PCT/EP2014/053485Google Scholar
- Grison C. Escarre J. (2011). Use of plant/its part having accumulated at least one metal having zinc, nickel or copper to prepare composition having a metal catalyst for allowing the implementation of organic synthesis reactions e.g. halogenation of alcohols. WO2011064462-A1Google Scholar
- Gupta R, Kumar V, Gupta M, Paul S, Gupta R (2008) Silica supported zinc chloride acetylation of amines alcohols and phenols. Indian J Chem 47B:1739–1743Google Scholar
- Horton S. Norris P. (1997). Preparative carbohydrate chemistry (Ed. Hanessian S.), Marcel Dekker, Inc., New York Basel.Google Scholar
- Kocienski PJ (1994) In: Enders D, Noyori R, Trost BM (eds) Protecting groups, Thieme Foundations of Organic Chemistry Series. Georg Thiem Verlag Stuttgart, New YorkGoogle Scholar
- Marsili R (2002) Flavor, fragrance, and odor analysis. Marcel Dekker, New YorkGoogle Scholar