Phosphorus, Sulfur, and Silicon and the Related Elements

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Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions

Touheeth Fatima, Govardhan Duguta, Venkanna Purugula, Hemanth Sriram Yelike & Chinna Rajanna Kamatala

To cite this article: Touheeth Fatima, Govardhan Duguta, Venkanna Purugula, Hemanth Sriram Yelike & Chinna Rajanna Kamatala (2020): Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions, Phosphorus, Sulfur, and Silicon and the Related Elements, DOI: 10.1080/10426507.2020.1782909 To link to this article: https://doi.org/10.1080/10426507.2020.1782909

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Cornforth and Corey-Suggs reagents as efficient catalysts for sulfonation of aromatic and heteroaromatic compounds using NaHSO3 under solvent free and microwave conditions

Touheeth Fatima, Govardhan Duguta, Venkanna Purugula, Hemanth Sriram Yelike, and Chinna Rajanna Kamatala Department of Chemistry, Osmania University, Hyderabad, Telangana, India

ABSTRACT ARTICLE HISTORY Cornforth and Corey-Suggs reagents Pyridinium Dichromate (PDC) and Pyridinium Chlorochromate Received 19 October 2019 (PCC) were explored as efficient catalysts for sulfonation of aromatic and heteroaromatic com- Accepted 10 June 2020 pounds using NaHSO in aqueous acetonitrile medium at room temperature within 1–4 h, while 3 KEYWORDS microwave assisted reactions took place within 1–4 min under solvent-free conditions. These Cornforth and Corey-Suggs observations indicate significant rate accelerations in microwave assisted reactions. which were reagents; PDC and PCC; explained due to the bulk activation of molecules induced by insitu generated high temperatures sulfonation of aromatic and and pressures when microwaves are transmitted through reaction medium. heteroaromatic compounds; microwave assisted GRAPHICAL ABSTRACT reactions; rate enhancements

Introduction compounds at room temperature.[23] The Katrizky research group took up an extensive sulfonation study The sulfonation of aromatic and heteroaromatic com- with a series of polycyclic aromatic and heteroaromatic pounds is one the foremost electrophilic aromatic substi- [24] compounds using SO3 in medium. In tution reactions, which involves the introduction of addition to the above certain recent reports revealed that electrophilic SO3 or (-SO3H) group onto an organo sulfur and phosphorus derivatives exhibited a [1–10] aromatic entity. Several reagents like sulfuric [25–29] – broad spectrum of biological activities. acid,[11,12] sulfur trioxide,[13 18] chlorosulfonic acid,[19] [30] – On the other hand, over the years, Cornforth and [20 22] [31,32] and silica supported sulfuric acid (Si-H2SO4) have Corey-Suggs reagents (Pyridinium dichromate or PDC, been explored for the sulfonation of aromatic compounds. and Pyridinium chlorochromate or PCC) have been used as Recently we have explored Vilsmeier-Haack adducts oxidizing agents and/or catalysts in a number of organic (DMF/POCl3,andDMF/SOCl2)togetherwithNaHSO3 as transformations to facilitate high product yields in reduced efficient reagents for the sulfonation of aromatic reaction times under acid free conditions, but have not been

CONTACT Chinna Rajanna Kamatala [email protected] Department of Chemistry, Osmania University, Hyderabad, Telangana 500 007, India. Supplemental data for this article is available online at https://doi.org/10.1080/10426507.2020.1782909. ß 2020 Taylor & Francis Group, LLC 2 T. FATIMA ET AL.

Y (i) Stirring at Room temperature Y PCC/ NaHSO3, Time:1 - 4 h PDC/ NaHSO , Time:1 - 4 h R 3 R

5 % (v/v) Acetonitrile in Water SO3H (ii) MWAS (Solvent -free) SO H R PCC/ NaHSO3,Time:1-4min R 3 PDC/ NaHSO ,Time:1-4min X 3 X

Where Y = H, OH, NH2 and other functional group; R = EWG or EDG X = N-H, O, S for Pyrrole, Furan and thiophene respectively

O O O

OHPy Cr O Cr OHPy Cl Cr OHPy O O O N Pyridinium Dichromate Pyridinium Chlorochromate Cornforth reagent (PDC) Corey-Suggs reagent (PCC) (Py)

Scheme 1. Sulfonation of aromatic and heteroaromatic compounds using PCC/NaHSO3 and PDC/NaHSO3.

Table 1. Optimization of catalyst quantity. extent. Therefore, all the other reactions were performed PCC/NaHSO3 PDC/NaHSO3 using (28 mmol) PCC/(16 mmol) PDC. The results are com- (Yield %) (Yield %) piled in Table 2, which show that the Cr (VI) reagent (PCC PCC PDC SN (mmol) Phenol Indole(mmol) Phenol Aniline Indole and PDC) almost exhibited the same catalytic efficiency, 1 9.28 60 62 62 5.28 62 70 63 with very good product yields, under conventional condi- 2 18.6 70 78 68 10.6 70 78 68 tions. Reactivity- selectivity principle was observed in the 3 27.9 75 80 71 15.9 73 86 70 present study even though reaction times did not appear to 4 37.2 75 82 74 21.2 75 86 73 5 46.5 75 82 74 26.5 75 86 72 follow strictly. Ortho substituted substrates afforded para- 6 55.8 75 82 74 31.8 75 86 73 substituted products, while para-substituted compounds resulted in ortho-substituted products. explored for sulfonation reactions. These features, together Under the optimized conditions, an array of aromatic with an aim of improving the conditions of sulfonation hydrocarbons, phenolic compounds, aromatic amines and het- eroaromatic compounds were used in the present study. A per- reactions, led us to explore these reagents (PDC and PCC) usal of the data compiled in Tables 2 and 3 reveal that PDC/ as eco-friendly catalysts for sulfonation of aromatic and het- NaHSO and PCC/NaHSO triggered sulfonation with aro- eroaromatic compounds using NaHSO under conventional 3 3 3 matic hydrocarbons, polycyclic aromatic compounds, phenolic and microwave assisted conditions. compounds, aromatic amines and heteroaromatic compounds, even though did not undergo sulfonation with these Results and discussion reagents. All the compounds afforded the corresponding sul- fonic acid derivatives, which were identified by IR, NMR spec- Aromatic and heteroaromatic compounds when treated with troscopy and mass spectrometry methods. The IR spectra of NaHSO3 and Cornforth reagent (PDC) or Corey-Suggs the isolated compounds indicated a band in the frequency reagent (PCC) in acetonitrile (MeCN) with continuous stir- range 1350–1342 cm 1,correspondingtoS¼Ostretching ring at room temperature for about 3 to 4 h, underwent sul- vibration, which revealed the presence of the sulfonic acid moi- fonation and afforded aryl sulfonic acids (Scheme 1). ety. The 1HNMR,13CNMR,andMSdataalongwithafew Initially we have tried to optimize the Cr (VI) quantity sample NMR spectra are also presented in the Supplemental before taking up the sulfonation reactions with hydroxyben- Materials (Figures S1–S6). Sulfonation of toluene afforded zene (phenol), phenylamine (aniline), and 1H-Indole 4-methyl benzene sulfonic acid (entry 1 in Tables 2 and 3)as (0.01 mol) as model substrates, with excess of NaHSO3 major component, while other aromatic compounds (entries 2 (0.02 mol). The reactions were performed for about 1–4h in to 9 in Tables 2 and 3) also gave corresponding sulfonic acid 5% (v/v) aqueous acetonitrile medium until the reactions were derivatives with very good yields. Phenols, substituted phenols, completed, as indicated by thin layer chromatography (TLC). and naphthol also afforded corresponding sulfonic acids in The observed results are compiled in Table 1.Excessof good yields within 1 to 4 h as shown in Tables 2 and 3 (entries NaHSO3 (0.02 mol) is used to facilitate the smooth reaction. 10–18). Heterocyclic compounds such indole and furan (entries Data presented in Table 1 shows that beyond 150 mg, the 19–22 in Tables 2 and 3), also underwent smooth sulfonation. catalyst (150 mg, 28 mmol PCC/150 mg, 16 mmol PDC) did Reaction times and product yields did not differ much when not further increase the product yield to any significant PCC/NaHSO3 is used in place of PDC/NaHSO3. PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS 3

Table 2. PDC/NaHSO3 mediated sulfonation of organic compounds under acid-free conditions. Conventional MWAS Entry Substrate Product R.T (h) Yield (%) R.T (min) Yield (%) 1 Methylbenzene 4-methylbenzene sulfonic acid 4.0 90 4.0 87 2 1,2-dimethylbenzene 3,4-dimethylbenzenesulfonic acid 3.0 82 2.5 93 3 1,3-dimethylbenzene 2,4-dimethylbenzenesulfonic acid 3.0 85 3.0 89 4 1,4-dimethylbenzene 2,5-dimethylbenzenesulfonic acid 2.0 88 2.0 81 5 Naphthalene Naphthalene-1-sulfonic acid 4.0 70 5.5 92 6 Chlorobenzene 4-chlorobenzenesulfonic acid 3.0 85 3.0 85 7 Bromobenzene 4-bromobenzenesulfonic acid 3.0 82 3.5 90 8 1,3,5-trimethylbenzene 2,4,6-trimethylbenzenesulfonic acid 2.0 80 4.0 93 9 9H-Carbazole Carbazole-3-sulfonic acid 5.0 65 4.0 72 10 Hydroxybenzene 4-hydroxybenzenesulfonic acid 2.0 75:20 1.0 80:17 11 Phenylamine 4-aminobenzenesulfonic acid 3.0 82 1.5 92 12 Methoxybenzene 4-methoxybenzenesulfonic acid 1.5 71:20 2.5 80:15 13 benzene-1,4-diol 2,5-dihydroxybenzenesulfonic acid 3.0 73:18 2.0 80:15 14 4-Nitrophenol 5-hydroxy-2-nitrobenzenesulfonic acid 2.0 81 1.0 89 15 4-Aminophenol 2-amino-5-hydroxybenzenesulfonic acid 2.5 77 1.5 86 16 1-Hydroxy-3-methylbenzene 5-hydroxy-2-methylbenzenesulfonic acid 3.0 66:18 2.0 77:16 17 benzene-1,2-diol 3,4-dihydroxybenzenesulfonic acid 2.5 81 1.5 90 18 3-hydroxychlorobenzene 2-chloro-4-hydroxybenzenesulfonic acid 2.0 69:14 2.0 70:20 19 1H-indole 1H-indole-4-sulfonic acid 3.0 74 2.5 83 20 1H-pyrrole 1H-pyrrole-4-sulfonic acid 2.0 73 2.0 82 21 Furan Furan-2-sulfonic acid 3.0 76 2.0 83 22 Dibenzothiophene Dibenzothiophene-2- sulfonic acid 4.0 75 2.5 70

Table 3. PCC/NaHSO3 mediated sulfonation of organic compounds under acid-free conditions. Conventional MWAS S.N Substrate Product R.T (h) Yield (%) R.T (min) Yield (%) 1 Methylbenzene 4-methylbenzene sulfonic acid 4.0 90 4.0 93 2 1,2-dimethylbenzene 3,4-dimethylbenzenesulfonic acid 3.0 82 3.0 85 3 1,3-dimethylbenzene 2,4-dimethylbenzenesulfonic acid 3.0 85 3.0 88 4 1,4-dimethylbenzene 2,5-dimethylbenzenesulfonic acid 2.0 88 2.0 90 5 Naphthalene Naphthalene-1-sulfonic acid 4.0 70 4.0 75 6 Chlorobenzene 4-chlorobenzenesulfonic acid 3.0 85 3.0 89 7 Bromobenzene 4-bromobenzenesulfonic acid 3.0 82 3.0 85 8 1,3,5-trimethylbenzene 2,4,6-trimethylbenzenesulfonic acid 2.0 80 2.0 84 9 9H-Carbazole Carbazole-3-sulfonic acid 5.0 65 5.0 68 10 Hydroxybenzene 4-hydroxybenzenesulfonic acid 2.0 75:16 1.0 78:20 11 Phenylamine 4-aminobenzenesulfonic acid 3.0 86 2.5 92 12 Methoxybenzene 4-methoxybenzenesulfonic acid 2.5 74:15 1.5 85:10 13 benzene-1,4-diol 2,5-dihydroxybenzenesulfonic acid 1.5 70:20 2.0 80:15 14 4-Nitrophenol 5-hydroxy-2-nitrobenzenesulfonic acid 2.5 92 1.5 90 15 4-Aminophenol 2-amino-5-hydroxybenzenesulfonic acid 1.5 76 2.0 84 16 1-Hydroxy-3-methylbenzene 5-hydroxy-2-methylbenzenesulfonic acid 2.0 69:18 1.0 72:18 17 benzene-1,2-diol 3,4-dihydroxybenzenesulfonic acid 3.0 87 2.0 90 18 3-hydroxychlorobenzene 2-chloro-4-hydroxybenzenesulfonic acid 2.5 63:15 1.5 70:20 19 1H-Indole 1H-indole-4-sulfonic acid 3.0 73 1.5 83 20 1H-Pyrrole 1H-pyrrole-4-sulfonic acid 2.5 76 2.0 82 21 Furan Furan-2-sulfonic acid 3.0 72 3.0 85 22 Dibenzothiophene Dibenzothiophene-2- sulfonic acid 4.0 75 4.0 79

Using green chemistry principles, put forward by pressure effects generated due to microwave propagation Anastas, Warner et al.[33,34] we have tried to improve the through the reaction mixture. overall ecofriendly nature of the reaction. We tried the In order to accomplish and enlighten the importance of reactions under solvent-free conditions in a microwave Cornforth (PDC) and Corey-Suggs (PCC) reagents in the oven as detailed in the experimental section. Reactions present study, observed data are compared with literature could be completed within 1–4 min, with enhanced product procedures as shown in Table 4, which reveal that the reac- yields. Structural variation with electron donating or with- tion times are less than literature procedures even in con- drawing groups in an aromatic compound did not indicate ventional methods, and further strengthen our contention much variation either in the reaction times or product that PDC and PCC could be used as catalysts safely for sul- yield. This observation may indicate cumulative effect of fonation of aromatic, polycyclic aromatic and heterocyc- both inductive and resonance effects in controlling the lic compounds. reactions. Highly significant rate accelerations in micro- The mechanism of the PDC/NaHSO3 induced sulfonation wave assisted reactions could be attributed to the bulk acti- reaction could be explained by considering the most plaus- – vation molecules,[35 40] which is triggered by direct and ible reactive species. In aqueous solutions, Cr (VI) is known uniform and fast heating of all the reactants, followed by to exist as several anionic, cationic and nonionic forms[41,42] 4 T. FATIMA ET AL.

Table 4. Comparative yields of sulfonation of aromatic compounds in present work with literature reports. Entry Catalyst/Reagent Substrate Reaction Conditions R.T. (%Yield) Ref. [12] 1 Conc.H2SO4 Methylbenzene 25 to 30 C / stirring 24.0 h 70 Sonication 45.0 min 100 2 PCC/NaHSO3 Methylbenzene Conventional 4.0 h 90 Present Work Microwave 4.0 min 93 PDC/NaHSO3 Methylbenzene Conventional 4.0 h 90 Microwave 4.0 min 87 [23] 3 (DMF-SOCl2)/NaHSO3 Hydroxybenzene Conventional 6.0 h 85 Sonication 3.0 h 88 (DMF–POCl3)/NaHSO3 Hydroxybenzene Conventional 5.5 h 88 Sonication 3.0 h 90 4 PCC/NaHSO3 Hydroxybenzene Conventional 2.0 h 75 Present Work Microwave 1.0 min 78 PDC/NaHSO3 Hydroxybenzene Conventional 2.0 h 75 Microwave 1.0 min 80 [22] 5 SiO2/HClO4 1H-Indole Conventional 4.0 h 76 Microwave 2.0 min 84 6 SiO2/H2SO4 1H-Indole Conventional 2.5 h 69 Microwave 5.0 min 73 7 PCC/NaHSO3 1H-Indole Conventional 3.0 h 73 Present Work Microwave 1.5 min 83 8 PDC/NaHSO3 1H-Indole Conventional 3.0 h 74 Microwave 2.5 min 83 [22] 7 SiO2/HClO4 1H-Pyrrole Conventional 3.5 h 71 Microwave 2.0 min 86 8 SiO2/H2SO4 1H-Pyrrole Conventional 3.5 h 68 Microwave 4.0 min 71 9 PCC/NaHSO3 1H-Pyrrole Conventional 2.5 h 76 Present Work Microwave 2.0 min 83 10 PDC/NaHSO3 1H-Pyrrole Conventional 2.0 h 73 Microwave 2.0 min 84

Scheme 2. Mechanism of PDC/NaHSO3 and PCC/NaHSO3 mediated thiocyanation of aromatic compounds.

– þ þ like HCrO4 ,H2CrO4, [HCrO3] and HCrO3B (where ðÞPyH Cr2O7 þ H2O 2½ðÞPyH ðÞHCrO4 (1) – – 2 B ¼ HSO , ClO ). It is well known that pyridinium dichro- 4 4 Alternatively, PDC may simply dissociate to afford mate (PDC) resembles K2Cr2O7. Therefore, similar types of þ [43,44] [(PyH) OCrO )] and [(PyH)OCrO ] as shown in the fol- species could be formulated. PDC upon hydrolysis may 3 2 þ - lowing equation, give pyridinium chromic acid ([(PyH) (HCrO4) ]) as shown ðÞ ½ðÞ þ½ðÞ þ in following reaction, PyH 2Cr2O7 PyH OCrO3 PyH OCrO2 (2) PHOSPHORUS, SULFUR, AND SILICON AND THE RELATED ELEMENTS 5

þ Active species [(PyH)OCrO2] thus formed may further until the temperature attains 100 C and 2 bar pressure). – react with bisulfite anion (HSO3 ) to afford [(PyH) OCrO2 After completion of the reaction as confirmed from TLC, (SO3H)], according to the following equation, the beaker containing the reaction mixture was removed, þ and worked up to isolate the product, as described in the ½ðÞPyHO CrO þ HSO ½ðÞPyH OCrO ðÞSO H (3) 2 3 2 3 previous section. The structures of the compounds were [(PyH)OCrO2(SO3H)] species thus formed probably characterized by physical and spectroscopic data, which are interacts with aromatic compound to result in aryl sulfonic in accordance with our earlier reports.[21,22] acid, as shown in Scheme 2. On the other hand, pyridinium chlorochromate (PCC) in Conclusions aqueous solutions may afford species like [(PyH) OCrO2Cl] þ and cationic [(PyH) OCrO(OH)Cl] species, which in turn In summary, in the present work we have accomplished may afford [(PyH)OCrO(OH)Cl(HSO3)] in situ in presence of – Cornforth and Corey-Suggs reagents (PDC and PCC) as excess of aqueous bisulfite (HSO3 ) as given in Equation 4. eco-friendly catalysts for sulfonation of aromatic and hetero- þ ðÞ aromatic compounds using NaHSO3 in aqueous acetonitrile ½ðÞPyH OCrO OH Cl þ HSO3 (4) medium at room temperature within 1–4 h, while microwave ½ðÞPyH OCrOðÞ OH ClðÞ HSO 3 assisted reactions took place within 1–3 min under solvent- Species thus formed which in turn supplements active free conditions. On the basis of the available literature, the electrophile during sulfonation of aromatic/heteroaromatic observed rate accelerations in MWAS reactions could be at compounds as shown in Scheme 2. best explained due to the bulk activation of molecules induced by microwave effects, which are transmitted through reaction medium at a time compares to conven- Experimental details tional heating. Materials and methods Reagent grade Acetonitrile (MeCN) was used as obtained Acknowledgments from supplier, while laboratory desktop water was distilled We are grateful to Head of the Chemistry Department, Osmania over alkaline permanganate and acid dichromate sequen- University Hyderabad for laboratory facilities and Professor P.K. tially. The purity of the PCC and PDC was checked by iodo- Saiprakash (former Dean, Science Faculty, O.U.) for constant metric method, according to standard procedures. encouragement. Chemicals used in this study were obtained from Avra (India), BDH- Merck (India), or SD (Fine Chemicals, India). Disclosure statement Bench mate model microwave oven (CEM-908010, 300 W) was used for microwave assisted reactions. No potential conflict of interest was reported by the authors.

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