General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis

Temperini, Andrea; Piazzolla, Francesca; Minuti, Lucio; Curini, Massimo; Siciliano, Carlo

doi:10.1021/acs.joc.7b00173

Cited by 66 publications

(32 citation statements)

References 99 publications

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“…It is important to underline that the reagents reported in the present work ( 1 , 2 , and 3 ) are more atom-efficient not only relative to the previously reported zinc-halo-selenates, but also among most of the alternative known methods for the synthesis of selenol esters. During the preparation of this manuscript a further synthesis of these compounds appeared starting from anhydrides, evidencing the current interest in this class of derivatives [24]. Nevertheless, in our opinion, both in terms of atom economy and general applicability, it can be claimed that the use of acyl chloride results largely preferable if compared to the anhydrides.…”

Section: Discussionmentioning

confidence: 90%

“…As a consequence of the increasing demand for selenol esters, the number of methods to prepare this class of compounds has been increased along the years [1,17,18,19,20,21,22,23,24,25,26,27,28,29,30,31,32,33,34,35,36,37,38,39,40,41,42,43] Among the strategies to prepare selenol esters there are the reactions of nucleophilic selenium reagents with an acyl group source, such as N -acyl benzotriazoles [17,18] activated carboxylic acids (using DCC [3] or PBu 3 [4,5,19,20]), enol esters [21], anhydrides [22,23,24], esters [25], carbon monoxide [26,27], aldehydes [28,29] or acyl chlorides [2,7,30,31,32,33,34,35,36,37,38,39,40,41,42,43]. Other approaches to selenol esters involve the alkylation of selenocarboxylate anions with alkyl h...…”

Section: Introductionmentioning

confidence: 99%

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Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under “On Water” Conditions

et al. 2017

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Section: Discussionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under “On Water” Conditions

et al. 2017

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“…Similarly, treatment of arylacetic acids with pivaloyl chloride (PivCl) would lead to an electrophilic intermediate 44.1 , which then reacted with N, O, or Se‐nucleophiles (Eq. 44‐1).…”

Section: Nucleophilic Acidsmentioning

confidence: 99%

Arylacetic Acids in Organic Synthesis

et al. 2019

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Arylacetic acids are widely used in organic reactions and their recent advances are summarized in six categories according to their triggered pathways: (1) the acid as directing group in ortho-or meta-CÀ H activation; (2) decarboxylation; (3) deprotonation; (4) nucleophilic methylenes; (5) nucleophilic acids; (6) electrophilic acids. Reactions with alkenes, alkynes, aldehydes, amines, water, Grignard reagents, silanes and so forth are discussed. We hope this Minireview will promote future research in this area. Recently, the Zeng group [3g] reported a weakly coordinationassisted alkynylation of arylacetic acids with iridium catalysis under air atmosphere (Eq. 2-2). It was supported the sixmembered ring cycloiridiated 2.5 acted as the key intermediate. The alkynylation of indole, thiophene, pyrrole, and benzo[b] thiophene afforded better yields than phenylacetic acids. The acid moiety could also participated in the intramolecular ortho-CÀ H activation, which was developed by the Shi group to obtain lactonization 2.6 (Eq. 2-3) (Scheme 2). Meta-CÀ H ArylationThe study of Yu group [3e] in 2017 revealed a successful control of meta selectivity 3.1 of arylation from aryl iodides (Eq. 3-1). The use of mono-protected 3-amino-2-hydroxypyridine (as ligand) and 2-carbomethoxynorbornene (NBE-CO 2 Me) were crucial. In the absence of NBE-CO 2 Me, only ortho-arylated product was obtained. This method was still efficient in a gramsale (Scheme 3). Decarboxylation Decarboxylative CouplingAs shown in Scheme 4, the decarboxylation could generate benzyl radicals 4.1. Then, direct couplings of 4.1 with diverse [ + ] These authors contributed equally. Scheme 1. Six categories based on triggered mechanism. 2 3 4 5 6 7 8 . Passerini Three-Component ReactionThe Passerini reaction was the oldest multicomponent reaction (MCR) [37d] in which isocyanides, carboxylic acids and aldehydes were used. It was powerful for the rapid construction of complex molecules. The tactic to expand the scope of Passerini reaction was to use surrogates of the carbonyl partners. As described in Scheme 51, syn-chlorooximes, [37b] diazoketones, [37c] alcohols, [37d,e] azirines [37f] and isatins [37g] could be employed instead of aryl or alkyl aldehydes [37a] (Scheme 51). Besides, in 2018, Zhang and co-workers [37] have firstly reported asymmetric phosphoric acid-catalyzed four-component Ugi reaction, which Scheme 45. BTM-catalyzed cycloaddition. Scheme 46. HBTM-catalyzed cycloaddition. Scheme 47. TFA-catalyzed reaction. Scheme 48. Friedel-Crafts triggered tandem reactions. Scheme 49. C-acylation of 1,3-diones. Scheme 50. C-acylation of 1,3-indandiones.

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“…[3] Accordingly, diverse organoselenyl esters with different acyl moieties have been synthesized. [4][5][6][7][8][9] For use as organoselenating reagents, variety at the organoselenyl groups is critical, which, however, has been limited to substituted phenyls and simple alkyls. Specifically, a scattered synthesis of heteroarylselenyl esters has been reported.…”

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confidence: 99%

“…Substituted phenylselenyl esters are conventionally synthesized via the reactions of acid chlorides/acid anhydrides and metal phenylselenoxides, which in turn are formed typically by NaBH 4 reduction of diphenyl diselenides. [4] The treatment of diselenides with strong reducing agents, however, was reported to induce deselenation in some cases. [3] Several modified methods have also been reported, which include selenoacid alkylation, [5] selenol acylation, [6] alkyne addition, [7] and aldehyde oxidation reactions.…”

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confidence: 99%

Rhodium‐Catalyzed Synthesis of Heteroarylselenyl Esters from Diheteroaryl Diselenides and Acid Fluorides

et al. 2020

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A rhodium complex catalyzed C−Se bond formation between diheteroaryl diselenides and acid fluorides in the presence of triphenylphosphine to provide heteroarylselenyl esters in good yields. The reaction was applicable to five‐ and six‐membered heteroaryl compounds. The heteroarylselenyl esters can be used as heteroaryselenating reagents in the synthesis of heteroaryl selenides, as shown by a platinum‐catalyzed addition reaction with 1‐octyne.

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General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis

Cited by 66 publications

References 99 publications

Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under “On Water” Conditions

Atom Efficient Preparation of Zinc Selenates for the Synthesis of Selenol Esters under “On Water” Conditions

Arylacetic Acids in Organic Synthesis

Rhodium‐Catalyzed Synthesis of Heteroarylselenyl Esters from Diheteroaryl Diselenides and Acid Fluorides

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