Application of trityl moieties in chemical processes: part I
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REVIEW
Application of trityl moieties in chemical processes: part I Saeed Baghery1 · Mahmoud Zarei1 · Mohammad Ali Zolfigol1 · Shadpour Mallakpour2 · Vajiheh Behranvand2 Received: 12 April 2020 / Accepted: 9 June 2020 © Iranian Chemical Society 2020
Abstract Triphenylcarbenium ions (trityl cations: [ RPh]3C+) are broadly identified organic compounds, because of their several uses, such as protective group, a catalyst for C–C bond formation, dye chemistry, carbohydrate chemistry, oxidation and reduction reagent, polymer and peptide synthesis, chiral catalyst, activity-based probes, and photochemical reactions. Trityl cations have also been applied as neutral Lewis acids in different chemical reactions. Possibly, the trityl cation is most widely used in hydride abstraction reactions both in the study of mechanisms transformations (organometallic and organic) and in organic syntheses. Ph3C+ is also extensively applied as very efficient activators and as one-electron oxidants for olefin polymerization reactions. In this review, we explain applications of trityl moieties in chemical processes and synthesis. Keywords Trityl moiety · Triphenylcarbenium ions · Trityl cations · Protective group · Trityl synthesis · Catalyst activity · Polymer and peptide synthesis
Introduction The triphenylmethyl (trityl; Trt or Tr) moiety was first presented by Helferich et al. [1], for the protection of the amino acids’ functional group in the production of peptides. The procedures of mixed anhydrides [2, 3] and activated esters [4] may be used to prepare trityl peptides. The same route may happen in the attendance of N,N′-dicyclohexylcarbodiimide (DCC) [5]. Velluz et al. [5] has successfully applied and studied the trityl moiety in reaction with the carbodiimide process for the preparation of oxytocin. This review is dedicated to Prof. Naser Iranpoor on the occasion of his 68th birthday. * Saeed Baghery [email protected] * Mahmoud Zarei [email protected] * Mohammad Ali Zolfigol [email protected]; [email protected] * Shadpour Mallakpour [email protected] 1
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan 6517838683, Islamic Republic of Iran
Department of Chemistry, Isfahan University of Technology, Isfahan 84156‑83111, Islamic Republic of Iran
2
For the protection of various functional groups such as thiols, amines, and alcohols in organic synthesis, triphenylmethyl moieties have been used [6]. Under various conditions, having reductive cleavage with Li/naphthalene in tetrahydrofuran (THF) the deprotection of the trityl group has been carried out [7, 8]. Several examples had been reported for the trityl group as a leaving group in inorganic synthesis [9]. An alcohol protecting group can be detected because it is easily removed when trifluoroacetic acid exists in dichloromethane to reproduce the alcohol [10]. Trityl moieties are appropriate protecting groups for chemoselective protection of numerous functional groups. As trityl ether is useful for the protection of primary
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