Description
Antonio Romerosaa, Franco Scalambraa, Pablo Lorenzo-Luisb.
a Área de Química Inorgánica-CIESOL. Univ. de Almería, 04071, Almería. Spain.
b Inorganic Chemistry Section, Chemistry Department, Faculty of Science, University of La Laguna, 38071 La Laguna, Tenerife, Spain.
Ruthenium complexes, water catalysis, metal allenylidenes.
Unsaturated carbenes, particularly the lower members, vinylidenes[1] and allenylidenes,[2] constitute a well established class of organometallic compounds which are attracting continuous increasing interest as they are useful reagents in both organic synthesis and homogeneous catalysis. Despite the ubiquitous character of transition-metal vinilydenes and allenylidenes not too many examples of these compounds soluble in water have been published until now despite of the the first example was presented in 2000.[3] This result is quite surprising given the intense research activity centered on such complexes [4] and the pressing request for environmentally benign technologies in the manufacture of fine chemicals.[5]
Herein, we report that water soluble allenylidyl complex [RuCp(C=C=CPh2)(mPTA)2](CF3SO3)3 (scheme) is capable of promoting the selective hydrolysis of enol-ethers. The reaction takes place in water and biphasic systems (CHCl3/water) in a short time (< 20 h) and exceedingly mild conditions (< 50 °C) leading to the catalytic synthesis of selective deuterated products.
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Table 1. Methatesis reactions of lineal and cyclic allyl ethers in D2O/CHCl3 catalysed by 1. Conditions: 20 mol% 1, D2O/CHCl3 1:1, 47ºC, 2.5 h, Ar, NMR tube.
REFERENCES
[1] M. I. Bruce, Chem. Rev., 1991, 91, 197. [2] M. I. Bruce, Chem. Rev., 1998, 98, 2797. [3] M. Saoud, A. Romerosa, M. Peruzzini, Organometallic, 2000, 19, 4005. [4] R. H. Grubbs, in Aqueous Organometallic Chemistry and Catalysis, I. T. Horváth, F. Joó, Eds.; NATO ASI Ser. 3 5; Kluwer Academic Publishers, Dordrecht, The Netherlands, 1995, p. 15.. [5] Manuel Serrano Ruiz, Chaker Lidrissi, Sonia Mañas, Maurizio Peruzzini, Antonio Romerosa. Journal Organomet. Chem. 2014, 751, 654-661. 50 aniversary special volume.
[1]: https://indico.esss.lu.se/event/756/picture/19.png
Primary author
Antonio Romerosa
(University of Almeria)
