Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides
We report an efficient alkynylation reaction of aryl iodides with simultaneous ortho-alkylaton of aryl rings. The reaction between three simple reagents—aryl halides, alkynes, and alkyl halides—formed aryl–alkynyl bonds carrying hindered aryl rings in one step. The reaction proceeded via a Catellani...
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| Format: | Journal Article |
| Language: | English |
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2016
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| Online Access: | https://hdl.handle.net/10356/80269 http://hdl.handle.net/10220/40513 |
| _version_ | 1826129680997023744 |
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| author | Lei, Chuanhu Jin, Xiaojia Zhou, Jianrong (Steve) |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Lei, Chuanhu Jin, Xiaojia Zhou, Jianrong (Steve) |
| author_sort | Lei, Chuanhu |
| collection | NTU |
| description | We report an efficient alkynylation reaction of aryl iodides with simultaneous ortho-alkylaton of aryl rings. The reaction between three simple reagents—aryl halides, alkynes, and alkyl halides—formed aryl–alkynyl bonds carrying hindered aryl rings in one step. The reaction proceeded via a Catellani-type pathway in the presence of norbornene. From a synthetic perspective, this reaction allows quick access toward many 1,2,3-substituted arenes and multiply substituted benzofurans, after manipulation of alkyne groups. These compounds are difficult to synthesize otherwise. |
| first_indexed | 2024-10-01T07:44:30Z |
| format | Journal Article |
| id | ntu-10356/80269 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T07:44:30Z |
| publishDate | 2016 |
| record_format | dspace |
| spelling | ntu-10356/802692020-03-07T12:31:21Z Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides Lei, Chuanhu Jin, Xiaojia Zhou, Jianrong (Steve) School of Physical and Mathematical Sciences alkynylation CH activation Catellani reaction benzofuran palladium catalysis We report an efficient alkynylation reaction of aryl iodides with simultaneous ortho-alkylaton of aryl rings. The reaction between three simple reagents—aryl halides, alkynes, and alkyl halides—formed aryl–alkynyl bonds carrying hindered aryl rings in one step. The reaction proceeded via a Catellani-type pathway in the presence of norbornene. From a synthetic perspective, this reaction allows quick access toward many 1,2,3-substituted arenes and multiply substituted benzofurans, after manipulation of alkyne groups. These compounds are difficult to synthesize otherwise. MOE (Min. of Education, S’pore) 2016-05-10T07:04:31Z 2019-12-06T13:46:13Z 2016-05-10T07:04:31Z 2019-12-06T13:46:13Z 2016 2016 Journal Article Lei, C., Jin, X., & Zhou, J. (2016). Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides. ACS Catalysis, 6(3), 1635-1639. 2155-5435 https://hdl.handle.net/10356/80269 http://hdl.handle.net/10220/40513 10.1021/acscatal.6b00169 191132 en ACS Catalysis © 2016 American Chemical Society. 5 p. |
| spellingShingle | alkynylation CH activation Catellani reaction benzofuran palladium catalysis Lei, Chuanhu Jin, Xiaojia Zhou, Jianrong (Steve) Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides |
| title | Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides |
| title_full | Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides |
| title_fullStr | Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides |
| title_full_unstemmed | Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides |
| title_short | Palladium-Catalyzed Alkynylation and Concomitant ortho Alkylation of Aryl Iodides |
| title_sort | palladium catalyzed alkynylation and concomitant ortho alkylation of aryl iodides |
| topic | alkynylation CH activation Catellani reaction benzofuran palladium catalysis |
| url | https://hdl.handle.net/10356/80269 http://hdl.handle.net/10220/40513 |
| work_keys_str_mv | AT leichuanhu palladiumcatalyzedalkynylationandconcomitantorthoalkylationofaryliodides AT jinxiaojia palladiumcatalyzedalkynylationandconcomitantorthoalkylationofaryliodides AT zhoujianrongsteve palladiumcatalyzedalkynylationandconcomitantorthoalkylationofaryliodides |