Electrophilic Halospirocyclization of N‑Benzylacrylamides to Access 4‑Halomethyl-2-azaspiro[4.5]decanes
An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast an...
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| Veröffentlicht in: | Journal of organic chemistry 2023-10, Vol.88 (19), p.13610-13621 |
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| container_end_page | 13621 |
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| container_issue | 19 |
| container_start_page | 13610 |
| container_title | Journal of organic chemistry |
| container_volume | 88 |
| creator | Zhang, Zhongyi Zhang, Wei Hou, Zhong-Wei Li, Pinhua Wang, Lei |
| description | An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize a wide variety of 4-halomethyl-2-azaspiro[4.5]decanes with satisfactory yields. The approach is further highlighted through gram-scale synthesis and diverse transformations of the spiro products. |
| doi_str_mv | 10.1021/acs.joc.3c01315 |
| format | Article |
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Org. Chem</addtitle><description>An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize a wide variety of 4-halomethyl-2-azaspiro[4.5]decanes with satisfactory yields. The approach is further highlighted through gram-scale synthesis and diverse transformations of the spiro products.</description><subject>ambient temperature</subject><subject>electrochemistry</subject><subject>Lewis acids</subject><subject>organic chemistry</subject><subject>photochemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFUT1PwzAQtRBIlMLMmhEJJfVnPsZSAUWqYIEJIctxHNXFiYOdDunEX-Av8ktwSVfEDe-G997p7h4AlwgmCGI0E9InGysTIiEiiB2BCWIYxmkB6TGYQIhxTHBKTsGZ9xsYijE2Ae-3Rsne2W6tjZbRUhjrO-2sHKTRO9Fr20a2jh6_P79uVLsbjJAuQKMr5aPeRnMplfcRDfze26h-PZgYx2Infue80oS9VUqKVvlzcFIL49XFoU_By93t82IZr57uHxbzVSwIJX1MWIFYKUWOAuC6hJkiWVYTpsqS4IrRnDKIyiovM1HJumKYlQUtIKwZrlKZkym4Gud2zn5sle95o71UxoQl7Nbz8B2S0jSD7F8pzlOSpRkp0iCdjVLprPdO1bxzuhFu4AjyfQI8JMBDAvyQQHBcj46R2Lo2XP2n-geUlYwx</recordid><startdate>20231006</startdate><enddate>20231006</enddate><creator>Zhang, Zhongyi</creator><creator>Zhang, Wei</creator><creator>Hou, Zhong-Wei</creator><creator>Li, Pinhua</creator><creator>Wang, Lei</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0001-6580-7671</orcidid><orcidid>https://orcid.org/0000-0002-8528-8087</orcidid></search><sort><creationdate>20231006</creationdate><title>Electrophilic Halospirocyclization of N‑Benzylacrylamides to Access 4‑Halomethyl-2-azaspiro[4.5]decanes</title><author>Zhang, Zhongyi ; Zhang, Wei ; Hou, Zhong-Wei ; Li, Pinhua ; Wang, Lei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a343t-35915bca81bca2fb07e377f35ebb32d5484501bd8b7adcfd525b94900f52d6c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>ambient temperature</topic><topic>electrochemistry</topic><topic>Lewis acids</topic><topic>organic chemistry</topic><topic>photochemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Zhongyi</creatorcontrib><creatorcontrib>Zhang, Wei</creatorcontrib><creatorcontrib>Hou, Zhong-Wei</creatorcontrib><creatorcontrib>Li, Pinhua</creatorcontrib><creatorcontrib>Wang, Lei</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Zhongyi</au><au>Zhang, Wei</au><au>Hou, Zhong-Wei</au><au>Li, Pinhua</au><au>Wang, Lei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrophilic Halospirocyclization of N‑Benzylacrylamides to Access 4‑Halomethyl-2-azaspiro[4.5]decanes</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2023-10-06</date><risdate>2023</risdate><volume>88</volume><issue>19</issue><spage>13610</spage><epage>13621</epage><pages>13610-13621</pages><issn>0022-3263</issn><issn>1520-6904</issn><eissn>1520-6904</eissn><abstract>An electrophilic spirocyclization of N-benzylacrylamides with N-halosuccinimides (NXS) as the halogenating reagents has been developed. This reaction is carried out at room temperature under simple conditions without relying on metal reagents, photochemistry, or electrochemistry, providing a fast and efficient route to synthesize a wide variety of 4-halomethyl-2-azaspiro[4.5]decanes with satisfactory yields. 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| issn | 0022-3263 1520-6904 1520-6904 |
| language | eng |
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| source | ACS Publications |
| subjects | ambient temperature electrochemistry Lewis acids organic chemistry photochemistry |
| title | Electrophilic Halospirocyclization of N‑Benzylacrylamides to Access 4‑Halomethyl-2-azaspiro[4.5]decanes |
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