Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols
We have developed a singlet oxygen (<sup>1</sup>O<sub>2</sub>)-mediated regioselective thiocyanation of terminal alkynes, indoles, pyrrole, anilines, and phenols using ammonium thiocyanate (NH<sub>4</sub>SCN) as an SCN source under visible light irradiation at roo...
محفوظ في:
| المؤلف الرئيسي: | |
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| مؤلفون آخرون: | , |
| منشور في: |
2024
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| الموضوعات: | |
| الوسوم: |
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| _version_ | 1852025825972453376 |
|---|---|
| author | Mahima Gupta (4173796) |
| author2 | Vaibhav Pramod Charpe (3748126) Kuo Chu Hwang (1780900) |
| author2_role | author author |
| author_facet | Mahima Gupta (4173796) Vaibhav Pramod Charpe (3748126) Kuo Chu Hwang (1780900) |
| author_role | author |
| dc.creator.none.fl_str_mv | Mahima Gupta (4173796) Vaibhav Pramod Charpe (3748126) Kuo Chu Hwang (1780900) |
| dc.date.none.fl_str_mv | 2024-10-21T06:15:15Z |
| dc.identifier.none.fl_str_mv | 10.1021/acssuschemeng.4c05654.s007 |
| dc.relation.none.fl_str_mv | https://figshare.com/articles/dataset/Singlet_Oxygen-Mediated_Regioselective_Thiocyanation_of_Terminal_Alkynes_Alkenes_Indoles_Pyrrole_Anilines_and_Phenols/27266383 |
| dc.rights.none.fl_str_mv | CC BY-NC 4.0 info:eu-repo/semantics/openAccess |
| dc.subject.none.fl_str_mv | Biophysics Biochemistry Microbiology Molecular Biology Physiology Ecology Developmental Biology Cancer Inorganic Chemistry Infectious Diseases Computational Biology Chemical Sciences not elsewhere classified visible light irradiation sup >•</ sup simple reaction setup scale evaluations signify energy visible light 1 </ sup regioselective thiocyanation protocol mediated regioselective thiocyanation respective thiocyanate products form thiocyanate products 4 </ sub 2 </ sub uses inexpensive nh phenols regioselectively form green chemistry metrics oxidative thiocyanation terminal alkynes singlet oxygen room temperature readily reacts method requires keto thiocyanates highly efficient environmentally feasible current oxidative |
| dc.title.none.fl_str_mv | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols |
| dc.type.none.fl_str_mv | Dataset info:eu-repo/semantics/publishedVersion dataset |
| description | We have developed a singlet oxygen (<sup>1</sup>O<sub>2</sub>)-mediated regioselective thiocyanation of terminal alkynes, indoles, pyrrole, anilines, and phenols using ammonium thiocyanate (NH<sub>4</sub>SCN) as an SCN source under visible light irradiation at room temperature. The oxidative thiocyanation of terminal alkynes forms α-keto thiocyanates, while indoles, pyrrole, anilines, and phenols regioselectively form the respective thiocyanate products. Herein, thiocyanate (SCN anion) undergoes single electron transfer (SET) by transferring an electron to singlet oxygen and forms an <sup>•</sup>SCN radical, which readily reacts with substrates to form thiocyanate products. Green chemistry metrics and Eco-scale evaluations signify that the current oxidative and regioselective thiocyanation protocol is an acceptable green organic synthesis process. Moreover, this method requires a simple reaction setup and uses inexpensive NH<sub>4</sub>SCN as an SCN source, O<sub>2</sub> as an oxidant, and low-energy visible light. Thus, the current oxidative thiocyanation process is mild, green, highly efficient, eco-friendly, and environmentally feasible. |
| eu_rights_str_mv | openAccess |
| id | Manara_8b2de52ddfea7b0ca2aa895b31ebcd44 |
| identifier_str_mv | 10.1021/acssuschemeng.4c05654.s007 |
| network_acronym_str | Manara |
| network_name_str | ManaraRepo |
| oai_identifier_str | oai:figshare.com:article/27266383 |
| publishDate | 2024 |
| repository.mail.fl_str_mv | |
| repository.name.fl_str_mv | |
| repository_id_str | |
| rights_invalid_str_mv | CC BY-NC 4.0 |
| spelling | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and PhenolsMahima Gupta (4173796)Vaibhav Pramod Charpe (3748126)Kuo Chu Hwang (1780900)BiophysicsBiochemistryMicrobiologyMolecular BiologyPhysiologyEcologyDevelopmental BiologyCancerInorganic ChemistryInfectious DiseasesComputational BiologyChemical Sciences not elsewhere classifiedvisible light irradiationsup >•</ supsimple reaction setupscale evaluations signifyenergy visible light1 </ supregioselective thiocyanation protocolmediated regioselective thiocyanationrespective thiocyanate productsform thiocyanate products4 </ sub2 </ subuses inexpensive nhphenols regioselectively formgreen chemistry metricsoxidative thiocyanationterminal alkynessinglet oxygenroom temperaturereadily reactsmethod requiresketo thiocyanateshighly efficientenvironmentally feasiblecurrent oxidativeWe have developed a singlet oxygen (<sup>1</sup>O<sub>2</sub>)-mediated regioselective thiocyanation of terminal alkynes, indoles, pyrrole, anilines, and phenols using ammonium thiocyanate (NH<sub>4</sub>SCN) as an SCN source under visible light irradiation at room temperature. The oxidative thiocyanation of terminal alkynes forms α-keto thiocyanates, while indoles, pyrrole, anilines, and phenols regioselectively form the respective thiocyanate products. Herein, thiocyanate (SCN anion) undergoes single electron transfer (SET) by transferring an electron to singlet oxygen and forms an <sup>•</sup>SCN radical, which readily reacts with substrates to form thiocyanate products. Green chemistry metrics and Eco-scale evaluations signify that the current oxidative and regioselective thiocyanation protocol is an acceptable green organic synthesis process. Moreover, this method requires a simple reaction setup and uses inexpensive NH<sub>4</sub>SCN as an SCN source, O<sub>2</sub> as an oxidant, and low-energy visible light. Thus, the current oxidative thiocyanation process is mild, green, highly efficient, eco-friendly, and environmentally feasible.2024-10-21T06:15:15ZDatasetinfo:eu-repo/semantics/publishedVersiondataset10.1021/acssuschemeng.4c05654.s007https://figshare.com/articles/dataset/Singlet_Oxygen-Mediated_Regioselective_Thiocyanation_of_Terminal_Alkynes_Alkenes_Indoles_Pyrrole_Anilines_and_Phenols/27266383CC BY-NC 4.0info:eu-repo/semantics/openAccessoai:figshare.com:article/272663832024-10-21T06:15:15Z |
| spellingShingle | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols Mahima Gupta (4173796) Biophysics Biochemistry Microbiology Molecular Biology Physiology Ecology Developmental Biology Cancer Inorganic Chemistry Infectious Diseases Computational Biology Chemical Sciences not elsewhere classified visible light irradiation sup >•</ sup simple reaction setup scale evaluations signify energy visible light 1 </ sup regioselective thiocyanation protocol mediated regioselective thiocyanation respective thiocyanate products form thiocyanate products 4 </ sub 2 </ sub uses inexpensive nh phenols regioselectively form green chemistry metrics oxidative thiocyanation terminal alkynes singlet oxygen room temperature readily reacts method requires keto thiocyanates highly efficient environmentally feasible current oxidative |
| status_str | publishedVersion |
| title | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols |
| title_full | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols |
| title_fullStr | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols |
| title_full_unstemmed | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols |
| title_short | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols |
| title_sort | Singlet Oxygen-Mediated Regioselective Thiocyanation of Terminal Alkynes, Alkenes, Indoles, Pyrrole, Anilines, and Phenols |
| topic | Biophysics Biochemistry Microbiology Molecular Biology Physiology Ecology Developmental Biology Cancer Inorganic Chemistry Infectious Diseases Computational Biology Chemical Sciences not elsewhere classified visible light irradiation sup >•</ sup simple reaction setup scale evaluations signify energy visible light 1 </ sup regioselective thiocyanation protocol mediated regioselective thiocyanation respective thiocyanate products form thiocyanate products 4 </ sub 2 </ sub uses inexpensive nh phenols regioselectively form green chemistry metrics oxidative thiocyanation terminal alkynes singlet oxygen room temperature readily reacts method requires keto thiocyanates highly efficient environmentally feasible current oxidative |