Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-Ones
In this study, we develop a concise and efficient synthetic strategy for the construction of eight-membered cyclic diaryl sulfides by undertaking [3+2] cycloaddition, 1,2-hydrogen shift, and C(sp<sup>2</sup>)-S bond cleavage steps on 2-methylenebenzothiophene-3-ones with aryne, using TBA...
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MDPI AG
2025-05-01
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| Online Access: | https://www.mdpi.com/2624-781X/6/2/35 |
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| author | Juhua Feng Wenjie Zou Haokun Zhang Qilin Huang Ailin Huang Kuan Liu Guizhou Yue |
| author_facet | Juhua Feng Wenjie Zou Haokun Zhang Qilin Huang Ailin Huang Kuan Liu Guizhou Yue |
| author_sort | Juhua Feng |
| collection | DOAJ |
| description | In this study, we develop a concise and efficient synthetic strategy for the construction of eight-membered cyclic diaryl sulfides by undertaking [3+2] cycloaddition, 1,2-hydrogen shift, and C(sp<sup>2</sup>)-S bond cleavage steps on 2-methylenebenzothiophene-3-ones with aryne, using TBAT as the fluorine source. This transformation proceeds well under mild conditions and affords the target products in high to excellent yields (up to 93% yields). The process provides a practical route to achieving sulfur-containing medium-sized heterocycles. |
| format | Article |
| id | doaj-art-4f783260bc444b1f9a4110e5c230fa17 |
| institution | DOAJ |
| issn | 2624-781X |
| language | English |
| publishDate | 2025-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Reactions |
| spelling | doaj-art-4f783260bc444b1f9a4110e5c230fa172025-08-20T03:16:38ZengMDPI AGReactions2624-781X2025-05-01623510.3390/reactions6020035Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-OnesJuhua Feng0Wenjie Zou1Haokun Zhang2Qilin Huang3Ailin Huang4Kuan Liu5Guizhou Yue6College of Science, Sichuan Agricultural University, Xinkang Road 46, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Xinkang Road 46, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Xinkang Road 46, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Xinkang Road 46, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Xinkang Road 46, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Xinkang Road 46, Ya’an 625014, ChinaCollege of Science, Sichuan Agricultural University, Xinkang Road 46, Ya’an 625014, ChinaIn this study, we develop a concise and efficient synthetic strategy for the construction of eight-membered cyclic diaryl sulfides by undertaking [3+2] cycloaddition, 1,2-hydrogen shift, and C(sp<sup>2</sup>)-S bond cleavage steps on 2-methylenebenzothiophene-3-ones with aryne, using TBAT as the fluorine source. This transformation proceeds well under mild conditions and affords the target products in high to excellent yields (up to 93% yields). The process provides a practical route to achieving sulfur-containing medium-sized heterocycles.https://www.mdpi.com/2624-781X/6/2/35aryne[3+2] cycloadditioneight-membered cyclic diaryl sulfides2-methylenebenzothiophene-3-ones |
| spellingShingle | Juhua Feng Wenjie Zou Haokun Zhang Qilin Huang Ailin Huang Kuan Liu Guizhou Yue Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-Ones Reactions aryne [3+2] cycloaddition eight-membered cyclic diaryl sulfides 2-methylenebenzothiophene-3-ones |
| title | Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-Ones |
| title_full | Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-Ones |
| title_fullStr | Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-Ones |
| title_full_unstemmed | Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-Ones |
| title_short | Efficient Synthesis of Eight-Membered Cyclic Diaryl Sulfides via an Aryne Reaction with 2-Methylenebenzothiophene-3-Ones |
| title_sort | efficient synthesis of eight membered cyclic diaryl sulfides via an aryne reaction with 2 methylenebenzothiophene 3 ones |
| topic | aryne [3+2] cycloaddition eight-membered cyclic diaryl sulfides 2-methylenebenzothiophene-3-ones |
| url | https://www.mdpi.com/2624-781X/6/2/35 |
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