Facile synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes via the FeCl<sub>3</sub>·6H<sub>2</sub>O-catalyzed two-step Friedel–Crafts-type reaction

Ruengsangtongkul, Sureeporn; Taprasert, P.; Sirion, Uthaiwan; Jaratjaroonphong, Jaray

doi:10.1039/c6ob01638c

Cited by 32 publications

(21 citation statements)

References 86 publications

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“…If such molecules are in solution, the surrounding solvent usually exerts an additional influence on their properties. For instance, the dependence of their reactivity [ 6 , 15 ], conformational preference [ 16 – 18 ], reaction kinetics [ 19 ] or spectroscopic properties [ 20 , 21 ] on the presence of a solvent and its polarity has been detected.…”

Section: Introductionmentioning

confidence: 99%

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Matczak

Domagała

2017

J Mol Model

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In this work several molecular properties of symmetrically disubstituted formaldehyde and thioformaldehyde have been studied using a quantum chemistry approach based on density functional theory. Five-membered heteroaromatic rings containing a single group 16 heteroatom were taken into account as the substituents (i.e., furan-2-yl, thiophen-2-yl, selenophen-2-yl, tellurophen-2-yl, and the experimentally as yet unknown polonophen-2-yl). For the resulting ten formaldehyde and thioformaldehyde derivatives, the geometry, energetics, frontier molecular orbitals, dipole moment and polarizability of their molecules were examined in order to establish the effect of ring heteroatom on these properties. Furthermore, these properties were also determined for the molecules in three solvents of low polarity (benzene, chloroform, and dichloromethane) in order to expand our study to include solvent effects. The dipole moment and polarizability of the investigated molecules show regular variations when the ring heteroatom descends through group 16 and the solvent polarity grows. The heteroatom and/or solvent effects on the part of the studied properties are, however, more complex. An attempt is made to rationalize the observed variations in the molecular properties. The conformational behavior of the investigated molecules was also explored and the conformationally weighted values of dipole moment and polarizability are presented. Graphical abstractSome molecular properties of symmetrically disubstituted formaldehyde and thioformaldehyde Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-017-3435-4) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Matczak

Domagała

2017

J Mol Model

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“…An atom‐economical room temperature synthesis of heteroaryl‐substituted TRAMs 29 utilizing FeCl 3 · 6H 2 O catalyst in DCE was developed by Jaratjaroonphong and his group (Scheme a) …”

Section: Synthesis Of Triarylmethanes (Trams)mentioning

confidence: 99%

Advances in The Catalytic Synthesis of Triarylmethanes (TRAMs)

2019

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The last couple of decades has witnessed an incredible development in the progress of catalytic creation of triarylmethane (TRAM) motif. The broad‐spectrum applications of TRAMs in domains like medicinal chemistry, pharmacology, dyes, and functional materials has urged scientists to invent their efficient synthetic strategies. Herein, we have attempted to comprehensively document the catalytic methodologies for the synthesis of triarylmethanes which will satiate the anticipations of the readers who are looking for an update and stimulate the researches for further development.

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“…Product 3a can be readily transformed into other interesting derivatives owing to the presence of functional groups (Scheme 3). Fore xample,i ndole addition to 3a using Bi(OTf) 3 (5 mol %) as aLewis acid [17] to trigger the formation of abenzyl cation intermediate gave 6 in 72 %yield as asingle diastereomer,t hus providing efficient access to naturalproduct-related biologically active compounds. [18] Moreover, by using PtO 2 ,t he endocyclic olefin was hydrogenated chemoselectively to give 7 in good yield without affecting the N-benzyl group.The carbamate functional group is ideally placed and can also serve as an anchorage point for selective transformations.T hus,t he treatment of 7 with TsOH·H 2 O afforded diene 8 in good yield with no change in the ee value.…”

Section: Angewandte Chemiementioning

confidence: 99%

Highly Diastereo‐ and Enantioselective Synthesis of Cyclohepta[b]indoles by Chiral‐Phosphoric‐Acid‐Catalyzed (4+3) Cycloaddition

et al. 2018

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Ah ighly enantio-and diastereoselective formal (4+ +3) cycloaddition of 1,3-diene-1-carbamates with 3-indolylmethanols in the presence of achiral phosphoric acid catalyst is reported. The approachd escribed herein provides efficient access to 6-aminotetrahydrocyclohepta [b]indoles in good yields with mostly complete diastereoselectivity and excellent levels of enantioselectivity (> 98:2 dr and up to 98 %ee). Mild reaction conditions,facile scale-up,and versatile derivatization highlight the practicality of this methodology.Amechanistic study suggests that cycloaddition occurs in astepwise fashion, after the formation of an ion pair between the chiral catalytic phosphate and the intermediate carbocation. Conflict of interestTheauthors declare no conflict of interest.

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Facile synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes via the FeCl₃·6H₂O-catalyzed two-step Friedel–Crafts-type reaction

Cited by 32 publications

References 86 publications

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Advances in The Catalytic Synthesis of Triarylmethanes (TRAMs)

Highly Diastereo‐ and Enantioselective Synthesis of Cyclohepta[b]indoles by Chiral‐Phosphoric‐Acid‐Catalyzed (4+3) Cycloaddition

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Facile synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes via the FeCl3·6H2O-catalyzed two-step Friedel–Crafts-type reaction

Cited by 32 publications

References 86 publications

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Heteroatom and solvent effects on molecular properties of formaldehyde and thioformaldehyde symmetrically disubstituted with heterocyclic groups C4H3Y (where Y = O–Po)

Advances in The Catalytic Synthesis of Triarylmethanes (TRAMs)

Highly Diastereo‐ and Enantioselective Synthesis of Cyclohepta[b]indoles by Chiral‐Phosphoric‐Acid‐Catalyzed (4+3) Cycloaddition

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Facile synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes via the FeCl₃·6H₂O-catalyzed two-step Friedel–Crafts-type reaction