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Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones
We disclosed a selective polychloromethylation and halogenation reaction of alkynes via a radical addition/spirocyclization cascade sequence, in which polyhaloalkanes were used as the precursor for polyhalomethyl and halogen radicals. Using this strategy, a series of valuable halogen-, CHCl 2 - or C...
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| Published in: | Organic & biomolecular chemistry 2022-08, Vol.20 (33), p.6659-6666 |
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| Main Authors: | , , , , , |
| Format: | Article |
| Language: | English |
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| cites | cdi_FETCH-LOGICAL-c292t-a5158fffc6d44cba80fdac0d9855b264d4649d3d3fc2c12e60eeec25be46e5a83 |
| container_end_page | 6666 |
| container_issue | 33 |
| container_start_page | 6659 |
| container_title | Organic & biomolecular chemistry |
| container_volume | 20 |
| creator | Li, Jun-Nan Li, Zi-Jie Shen, Liu-Yu Li, Pinhua Zhang, Yicheng Yang, Wen-Chao |
| description | We disclosed a selective polychloromethylation and halogenation reaction of alkynes
via
a radical addition/spirocyclization cascade sequence, in which polyhaloalkanes were used as the precursor for polyhalomethyl and halogen radicals. Using this strategy, a series of valuable halogen-, CHCl
2
- or CCl
3
-containing spiro[5,5]trienones were synthesized in good yields with good functional group tolerance in one pot under simple and mild conditions. It is noted that an unprecedented halogenation instead of dibromomethylation was achieved when CH
2
Br
2
was used in this work. |
| doi_str_mv | 10.1039/d2ob01053d |
| format | article |
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via
a radical addition/spirocyclization cascade sequence, in which polyhaloalkanes were used as the precursor for polyhalomethyl and halogen radicals. Using this strategy, a series of valuable halogen-, CHCl
2
- or CCl
3
-containing spiro[5,5]trienones were synthesized in good yields with good functional group tolerance in one pot under simple and mild conditions. It is noted that an unprecedented halogenation instead of dibromomethylation was achieved when CH
2
Br
2
was used in this work.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob01053d</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alkynes ; CCL3 protein ; Functional groups ; Halogenation</subject><ispartof>Organic & biomolecular chemistry, 2022-08, Vol.20 (33), p.6659-6666</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c292t-a5158fffc6d44cba80fdac0d9855b264d4649d3d3fc2c12e60eeec25be46e5a83</citedby><cites>FETCH-LOGICAL-c292t-a5158fffc6d44cba80fdac0d9855b264d4649d3d3fc2c12e60eeec25be46e5a83</cites><orcidid>0000-0002-8528-8087 ; 0000-0001-7729-7365</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Li, Jun-Nan</creatorcontrib><creatorcontrib>Li, Zi-Jie</creatorcontrib><creatorcontrib>Shen, Liu-Yu</creatorcontrib><creatorcontrib>Li, Pinhua</creatorcontrib><creatorcontrib>Zhang, Yicheng</creatorcontrib><creatorcontrib>Yang, Wen-Chao</creatorcontrib><title>Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones</title><title>Organic & biomolecular chemistry</title><description>We disclosed a selective polychloromethylation and halogenation reaction of alkynes
via
a radical addition/spirocyclization cascade sequence, in which polyhaloalkanes were used as the precursor for polyhalomethyl and halogen radicals. Using this strategy, a series of valuable halogen-, CHCl
2
- or CCl
3
-containing spiro[5,5]trienones were synthesized in good yields with good functional group tolerance in one pot under simple and mild conditions. It is noted that an unprecedented halogenation instead of dibromomethylation was achieved when CH
2
Br
2
was used in this work.</description><subject>Alkynes</subject><subject>CCL3 protein</subject><subject>Functional groups</subject><subject>Halogenation</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpdkU9LxDAQxYsouK5e_AQFLyJWkzRpm6Pu-g8W9qCeREqaTG2WbFKT7kr99HZ3xYOneTP83jDDi6JTjK4wSvm1Iq5CGLFU7UUjTPM8GTTf_9MEHUZHISwQwjzP6Cj6eu5t10DQIXZ13DrTy8Y475bQNb0RHahYWBU3wrgPsNs-tNq7N3bJ3juvwToLIV5rESsQg090eg07RvbS6O9h4OxmeaWF703cbx3H0UEtTICT3zqOXu_vXiaPyWz-8DS5mSWScNIlgmFW1HUtM0WprESBaiUkUrxgrCIZVTSjXKUqrSWRmECGAEASVgHNgIkiHUfnu72td58rCF251EGCMcKCW4WSZJxzVmBKB_TsH7pwK2-H60qSI5YXDGV8oC52lPQuBA912Xq9HD4rMSo3GZRTMr_dZjBNfwDfY30j</recordid><startdate>20220824</startdate><enddate>20220824</enddate><creator>Li, Jun-Nan</creator><creator>Li, Zi-Jie</creator><creator>Shen, Liu-Yu</creator><creator>Li, Pinhua</creator><creator>Zhang, Yicheng</creator><creator>Yang, Wen-Chao</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8528-8087</orcidid><orcidid>https://orcid.org/0000-0001-7729-7365</orcidid></search><sort><creationdate>20220824</creationdate><title>Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones</title><author>Li, Jun-Nan ; Li, Zi-Jie ; Shen, Liu-Yu ; Li, Pinhua ; Zhang, Yicheng ; Yang, Wen-Chao</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c292t-a5158fffc6d44cba80fdac0d9855b264d4649d3d3fc2c12e60eeec25be46e5a83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkynes</topic><topic>CCL3 protein</topic><topic>Functional groups</topic><topic>Halogenation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jun-Nan</creatorcontrib><creatorcontrib>Li, Zi-Jie</creatorcontrib><creatorcontrib>Shen, Liu-Yu</creatorcontrib><creatorcontrib>Li, Pinhua</creatorcontrib><creatorcontrib>Zhang, Yicheng</creatorcontrib><creatorcontrib>Yang, Wen-Chao</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Jun-Nan</au><au>Li, Zi-Jie</au><au>Shen, Liu-Yu</au><au>Li, Pinhua</au><au>Zhang, Yicheng</au><au>Yang, Wen-Chao</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2022-08-24</date><risdate>2022</risdate><volume>20</volume><issue>33</issue><spage>6659</spage><epage>6666</epage><pages>6659-6666</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>We disclosed a selective polychloromethylation and halogenation reaction of alkynes
via
a radical addition/spirocyclization cascade sequence, in which polyhaloalkanes were used as the precursor for polyhalomethyl and halogen radicals. Using this strategy, a series of valuable halogen-, CHCl
2
- or CCl
3
-containing spiro[5,5]trienones were synthesized in good yields with good functional group tolerance in one pot under simple and mild conditions. It is noted that an unprecedented halogenation instead of dibromomethylation was achieved when CH
2
Br
2
was used in this work.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2ob01053d</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0002-8528-8087</orcidid><orcidid>https://orcid.org/0000-0001-7729-7365</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2022-08, Vol.20 (33), p.6659-6666 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2699958144 |
| source | Royal Society of Chemistry |
| subjects | Alkynes CCL3 protein Functional groups Halogenation |
| title | Synthesis of polychloromethylated and halogenated spiro[5,5]trienones via dearomative spirocyclization of biaryl ynones |
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