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Recent progress in nickel-catalyzed carboboration of alkenes
Alkenes represent one of the most useful building blocks for organic synthesis, owing to their abundance and versatile reactivity. Transition metal (Pd, Cu, Co, Ni, Fe, etc .) catalyzed difunctionalization of alkenes provides efficient access to substituted molecules from readily available alkenes b...
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| Published in: | Organic & biomolecular chemistry 2022-12, Vol.2 (47), p.9255-9271 |
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| container_end_page | 9271 |
| container_issue | 47 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Ye, Yang Lin, Ying Mao, Nian-Dong Yang, Huimin Ye, Xiang-Yang Xie, Tian |
| description | Alkenes represent one of the most useful building blocks for organic synthesis, owing to their abundance and versatile reactivity. Transition metal (Pd, Cu, Co, Ni, Fe,
etc
.) catalyzed difunctionalization of alkenes provides efficient access to substituted molecules from readily available alkenes by installing functional groups across their carbon-carbon double bonds. Particularly, Nickel-based catalytic complexes have attracted a great deal of attention. This is because they are prone to undergoing oxidative addition and slow β-hydride elimination, and can access both two-electron and radical pathways. Numerous elegant Ni-catalyzed cross-coupling methods,
e.g.
, (hetero)arylboration, alkenylboration, alkylboration and alkynylboration of alkenes, have been developed with broad scopes and a high tolerance to a variety of functional groups. Therefore, the Ni-catalyzed carboboration of alkenes has become an efficient synthetic protocol to deliver substituted compounds by the cross-coupling of alkenes, electrophiles, and B
2
Pin
2
. Despite this progress, a number of challenging issues remaining in the field include broadening the types of carboboration reactions, especially the asymmetric ones, diversifying electrophile types (which is limited to halogens for now) and gaining profound insight into the reaction mechanisms. This review summarizes the recent progress in this emerging field from the literature published since 2018. It will provide the scientific community with convenience to access collective information and to accelerate their further research in order to broaden the scope of methodology and application in drug discovery programs.
This Review provides the community with a comprehensive summary of the application of the Ni-catalyzed carboboration strategy by carefully classifying the reaction types and detailing useful examples. |
| doi_str_mv | 10.1039/d2ob01855a |
| format | article |
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etc
.) catalyzed difunctionalization of alkenes provides efficient access to substituted molecules from readily available alkenes by installing functional groups across their carbon-carbon double bonds. Particularly, Nickel-based catalytic complexes have attracted a great deal of attention. This is because they are prone to undergoing oxidative addition and slow β-hydride elimination, and can access both two-electron and radical pathways. Numerous elegant Ni-catalyzed cross-coupling methods,
e.g.
, (hetero)arylboration, alkenylboration, alkylboration and alkynylboration of alkenes, have been developed with broad scopes and a high tolerance to a variety of functional groups. Therefore, the Ni-catalyzed carboboration of alkenes has become an efficient synthetic protocol to deliver substituted compounds by the cross-coupling of alkenes, electrophiles, and B
2
Pin
2
. Despite this progress, a number of challenging issues remaining in the field include broadening the types of carboboration reactions, especially the asymmetric ones, diversifying electrophile types (which is limited to halogens for now) and gaining profound insight into the reaction mechanisms. This review summarizes the recent progress in this emerging field from the literature published since 2018. It will provide the scientific community with convenience to access collective information and to accelerate their further research in order to broaden the scope of methodology and application in drug discovery programs.
This Review provides the community with a comprehensive summary of the application of the Ni-catalyzed carboboration strategy by carefully classifying the reaction types and detailing useful examples.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob01855a</identifier><identifier>PMID: 36399007</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alkenes ; Carbon ; Copper ; Coupling (molecular) ; Coupling methods ; Cross coupling ; Functional groups ; Halogens ; Iron ; Nickel ; Palladium ; Reaction mechanisms ; Substitutes ; Transition metals</subject><ispartof>Organic & biomolecular chemistry, 2022-12, Vol.2 (47), p.9255-9271</ispartof><rights>Copyright Royal Society of Chemistry 2022</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-2fa49eaba9fc63bad9145567cc61571e2620ecbe8c77a181b61ea7250b4a8fa63</citedby><cites>FETCH-LOGICAL-c337t-2fa49eaba9fc63bad9145567cc61571e2620ecbe8c77a181b61ea7250b4a8fa63</cites><orcidid>0000-0001-5279-8104 ; 0000-0003-3739-0930</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,786,790,27957,27958</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36399007$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ye, Yang</creatorcontrib><creatorcontrib>Lin, Ying</creatorcontrib><creatorcontrib>Mao, Nian-Dong</creatorcontrib><creatorcontrib>Yang, Huimin</creatorcontrib><creatorcontrib>Ye, Xiang-Yang</creatorcontrib><creatorcontrib>Xie, Tian</creatorcontrib><title>Recent progress in nickel-catalyzed carboboration of alkenes</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Alkenes represent one of the most useful building blocks for organic synthesis, owing to their abundance and versatile reactivity. Transition metal (Pd, Cu, Co, Ni, Fe,
etc
.) catalyzed difunctionalization of alkenes provides efficient access to substituted molecules from readily available alkenes by installing functional groups across their carbon-carbon double bonds. Particularly, Nickel-based catalytic complexes have attracted a great deal of attention. This is because they are prone to undergoing oxidative addition and slow β-hydride elimination, and can access both two-electron and radical pathways. Numerous elegant Ni-catalyzed cross-coupling methods,
e.g.
, (hetero)arylboration, alkenylboration, alkylboration and alkynylboration of alkenes, have been developed with broad scopes and a high tolerance to a variety of functional groups. Therefore, the Ni-catalyzed carboboration of alkenes has become an efficient synthetic protocol to deliver substituted compounds by the cross-coupling of alkenes, electrophiles, and B
2
Pin
2
. Despite this progress, a number of challenging issues remaining in the field include broadening the types of carboboration reactions, especially the asymmetric ones, diversifying electrophile types (which is limited to halogens for now) and gaining profound insight into the reaction mechanisms. This review summarizes the recent progress in this emerging field from the literature published since 2018. It will provide the scientific community with convenience to access collective information and to accelerate their further research in order to broaden the scope of methodology and application in drug discovery programs.
This Review provides the community with a comprehensive summary of the application of the Ni-catalyzed carboboration strategy by carefully classifying the reaction types and detailing useful examples.</description><subject>Alkenes</subject><subject>Carbon</subject><subject>Copper</subject><subject>Coupling (molecular)</subject><subject>Coupling methods</subject><subject>Cross coupling</subject><subject>Functional groups</subject><subject>Halogens</subject><subject>Iron</subject><subject>Nickel</subject><subject>Palladium</subject><subject>Reaction mechanisms</subject><subject>Substitutes</subject><subject>Transition metals</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNpd0U1Lw0AQBuBFFKvVi3cl4EWE6H4ku1nwUusnFAqi5zC7mUjaNFt3k0P99UZbK3iagXkYhncIOWH0ilGhrwvuDGVZmsIOOWCJUjFNhd7d9pwOyGEIM0qZVjLZJwMhhdaUqgNy84IWmzZaevfuMYSoaqKmsnOsYwst1KtPLCIL3jjjPLSVayJXRlDPscFwRPZKqAMeb-qQvD3cv46f4sn08Xk8msRWCNXGvIREIxjQpZXCQKFZkqZSWStZqhhyySlag5lVCljGjGQIiqfUJJCVIMWQXKz39ld-dBjafFEFi3UNDbou5FyJjOmEZbSn5__ozHW-6a_rVaI4E6lMenW5Vta7EDyW-dJXC_CrnNH8O9P8jk9vfzId9fhss7IzCyy29DfEHpyugQ92O_17ivgCyE96bg</recordid><startdate>20221207</startdate><enddate>20221207</enddate><creator>Ye, Yang</creator><creator>Lin, Ying</creator><creator>Mao, Nian-Dong</creator><creator>Yang, Huimin</creator><creator>Ye, Xiang-Yang</creator><creator>Xie, Tian</creator><general>Royal Society of Chemistry</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><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/0000-0001-5279-8104</orcidid><orcidid>https://orcid.org/0000-0003-3739-0930</orcidid></search><sort><creationdate>20221207</creationdate><title>Recent progress in nickel-catalyzed carboboration of alkenes</title><author>Ye, Yang ; Lin, Ying ; Mao, Nian-Dong ; Yang, Huimin ; Ye, Xiang-Yang ; Xie, Tian</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-2fa49eaba9fc63bad9145567cc61571e2620ecbe8c77a181b61ea7250b4a8fa63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Alkenes</topic><topic>Carbon</topic><topic>Copper</topic><topic>Coupling (molecular)</topic><topic>Coupling methods</topic><topic>Cross coupling</topic><topic>Functional groups</topic><topic>Halogens</topic><topic>Iron</topic><topic>Nickel</topic><topic>Palladium</topic><topic>Reaction mechanisms</topic><topic>Substitutes</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ye, Yang</creatorcontrib><creatorcontrib>Lin, Ying</creatorcontrib><creatorcontrib>Mao, Nian-Dong</creatorcontrib><creatorcontrib>Yang, Huimin</creatorcontrib><creatorcontrib>Ye, Xiang-Yang</creatorcontrib><creatorcontrib>Xie, Tian</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><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>Ye, Yang</au><au>Lin, Ying</au><au>Mao, Nian-Dong</au><au>Yang, Huimin</au><au>Ye, Xiang-Yang</au><au>Xie, Tian</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Recent progress in nickel-catalyzed carboboration of alkenes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2022-12-07</date><risdate>2022</risdate><volume>2</volume><issue>47</issue><spage>9255</spage><epage>9271</epage><pages>9255-9271</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><notes>Ms Yang is currently a first year student working on her Master degree at Hangzhou Normal University. Her research interests focus on organic synthesis methodology.</notes><notes>Dr Tian Xie is currently a professor of the School of Pharmacy and Holistic Integrative Oncology Institutes at Hangzhou Normal University. He is also the director of the Key Laboratory of Elemene Class Anti-cancer Chinese Medicine of Zhejiang Province and the head of the Engineering Laboratory of Development and Application of Traditional Chinese Medicine from Zhejiang Province. Dr Xie has been engaged in research, teaching and industrialization of Chinese and Western Medicine, natural medicine research and development, targeted liposomes development, pharmaceutical engineering, and green chemistry for more than 40 years.</notes><notes>Mr Lin is currently a second year student working on his Master degree at Hangzhou Normal University. His research interests focus on organic synthesis methodology.</notes><notes>Dr Xiang-Yang Ye obtained his Ph.D. in 1999 from The University of Hong Kong under the supervision of Prof. Dan Yang. He then spent 3 years at Princeton University as a postdoc researcher. From 2002 to 2016, he worked in the Pharmaceutical Research Institute at Bristol-Myers Squibb Company, first as Research Investigator and ultimately promoted to Principal Scientist. Since December 2018, he has been a professor at Hangzhou Normal University. His research interests center on drug discovery in the field of oncology, metabolic diseases, and immunology.</notes><notes>Mr Mao is currently a third year student working on his Master degree at Hangzhou Normal University. His research interests center on drug discovery.</notes><notes>Dr Yang Ye obtained his Ph.D. in 2020 from Shanghai University (with Prof. Hegui Gong). Then he joined the faculty at the School of Pharmacy, Hangzhou Normal University in September 2021. His research interests focus on the development of synthetic methodology, reductive cross-coupling, asymmetric catalysis, and the application of these methods in drug discovery programs.</notes><notes>ObjectType-Article-2</notes><notes>SourceType-Scholarly Journals-1</notes><notes>ObjectType-Feature-3</notes><notes>content type line 23</notes><notes>ObjectType-Review-1</notes><abstract>Alkenes represent one of the most useful building blocks for organic synthesis, owing to their abundance and versatile reactivity. Transition metal (Pd, Cu, Co, Ni, Fe,
etc
.) catalyzed difunctionalization of alkenes provides efficient access to substituted molecules from readily available alkenes by installing functional groups across their carbon-carbon double bonds. Particularly, Nickel-based catalytic complexes have attracted a great deal of attention. This is because they are prone to undergoing oxidative addition and slow β-hydride elimination, and can access both two-electron and radical pathways. Numerous elegant Ni-catalyzed cross-coupling methods,
e.g.
, (hetero)arylboration, alkenylboration, alkylboration and alkynylboration of alkenes, have been developed with broad scopes and a high tolerance to a variety of functional groups. Therefore, the Ni-catalyzed carboboration of alkenes has become an efficient synthetic protocol to deliver substituted compounds by the cross-coupling of alkenes, electrophiles, and B
2
Pin
2
. Despite this progress, a number of challenging issues remaining in the field include broadening the types of carboboration reactions, especially the asymmetric ones, diversifying electrophile types (which is limited to halogens for now) and gaining profound insight into the reaction mechanisms. This review summarizes the recent progress in this emerging field from the literature published since 2018. It will provide the scientific community with convenience to access collective information and to accelerate their further research in order to broaden the scope of methodology and application in drug discovery programs.
This Review provides the community with a comprehensive summary of the application of the Ni-catalyzed carboboration strategy by carefully classifying the reaction types and detailing useful examples.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36399007</pmid><doi>10.1039/d2ob01855a</doi><tpages>17</tpages><orcidid>https://orcid.org/0000-0001-5279-8104</orcidid><orcidid>https://orcid.org/0000-0003-3739-0930</orcidid></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2022-12, Vol.2 (47), p.9255-9271 |
| issn | 1477-0520 1477-0539 |
| language | eng |
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| source | Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list) |
| subjects | Alkenes Carbon Copper Coupling (molecular) Coupling methods Cross coupling Functional groups Halogens Iron Nickel Palladium Reaction mechanisms Substitutes Transition metals |
| title | Recent progress in nickel-catalyzed carboboration of alkenes |
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