Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes
A nickel‐catalyzed cross‐coupling between (hetero)arylborons and unactivated 1‐bromo‐1,1‐difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine‐based ligand, 4,4′‐ditBu‐bpy, and a monodentate pyridine‐based ligand, DMAP) offers a highly efficient nickel‐based catalytic sy...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2016-05, Vol.55 (19), p.5837-5841 |
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| creator | Xiao, Yu-Lan Min, Qiao-Qiao Xu, Chang Wang, Ruo-Wen Zhang, Xingang |
| description | A nickel‐catalyzed cross‐coupling between (hetero)arylborons and unactivated 1‐bromo‐1,1‐difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine‐based ligand, 4,4′‐ditBu‐bpy, and a monodentate pyridine‐based ligand, DMAP) offers a highly efficient nickel‐based catalytic system to prepare difluoroalkylated arenes which have important applications in medicinal chemistry.
Ligand combo: The title reaction requires the use of a combined (2+1) ligand system, that is, a combination of a bi‐ and monodentate ligand (4,4′‐ditBu‐bpy + DMAP). This system allows employment of a wide range of unactivated 1‐bromo‐1,1‐difluoroalkanes as coupling partners, thus providing a highly efficient method for applications in drug discovery and development. bpy=bipyridine, DMAP=4‐(N,N‐dimethylamino)pyridine. |
| doi_str_mv | 10.1002/anie.201601351 |
| format | Article |
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Ligand combo: The title reaction requires the use of a combined (2+1) ligand system, that is, a combination of a bi‐ and monodentate ligand (4,4′‐ditBu‐bpy + DMAP). This system allows employment of a wide range of unactivated 1‐bromo‐1,1‐difluoroalkanes as coupling partners, thus providing a highly efficient method for applications in drug discovery and development. bpy=bipyridine, DMAP=4‐(N,N‐dimethylamino)pyridine.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.201601351</identifier><identifier>PMID: 27060704</identifier><identifier>CODEN: ACIEAY</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>arenes ; cross-coupling ; fluorine ; ligand design ; Ligands ; nickel</subject><ispartof>Angewandte Chemie International Edition, 2016-05, Vol.55 (19), p.5837-5841</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4481-55ef25be89732086c7e8a0fad0a78140791905114b2172ca21336c2ed5e623a53</citedby><cites>FETCH-LOGICAL-c4481-55ef25be89732086c7e8a0fad0a78140791905114b2172ca21336c2ed5e623a53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.201601351$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.201601351$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27060704$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Xiao, Yu-Lan</creatorcontrib><creatorcontrib>Min, Qiao-Qiao</creatorcontrib><creatorcontrib>Xu, Chang</creatorcontrib><creatorcontrib>Wang, Ruo-Wen</creatorcontrib><creatorcontrib>Zhang, Xingang</creatorcontrib><title>Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes</title><title>Angewandte Chemie International Edition</title><addtitle>Angew. Chem. Int. Ed</addtitle><description>A nickel‐catalyzed cross‐coupling between (hetero)arylborons and unactivated 1‐bromo‐1,1‐difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine‐based ligand, 4,4′‐ditBu‐bpy, and a monodentate pyridine‐based ligand, DMAP) offers a highly efficient nickel‐based catalytic system to prepare difluoroalkylated arenes which have important applications in medicinal chemistry.
Ligand combo: The title reaction requires the use of a combined (2+1) ligand system, that is, a combination of a bi‐ and monodentate ligand (4,4′‐ditBu‐bpy + DMAP). This system allows employment of a wide range of unactivated 1‐bromo‐1,1‐difluoroalkanes as coupling partners, thus providing a highly efficient method for applications in drug discovery and development. bpy=bipyridine, DMAP=4‐(N,N‐dimethylamino)pyridine.</description><subject>arenes</subject><subject>cross-coupling</subject><subject>fluorine</subject><subject>ligand design</subject><subject>Ligands</subject><subject>nickel</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkc9v0zAYhi0EYj_gyhFF4jIkXL7PjmPnWLqxTprKhWlHy00c4dWNh50wsr8eVx0FceFkS37eR6_8EvIGYYYA7KPpnZ0xwAqQC3xGjlEwpFxK_jzfS86pVAKPyElKd5lXCqqX5IhJqEBCeUy6lWs21tOFGYyfHm1bnLvOjyEG4zeTN4MLfRG64mxpBxvD-3mc_Dq_9ql4cMO34qY3zeB-mCEnkX6KYRsofkDa_rGY3qZX5EVnfLKvn85TcvP54utiSa-_XF4t5te0KUuFVAjbMbG2qpacgaoaaZWBzrRgpMISZI01CMRyzVCyxjDkvGqYbYWtGDeCn5Kzvfc-hu-jTYPeutRY73OJMCaNUpWyrBF26Lt_0Lswxj6321G8VjWAytRsTzUxpBRtp--j25o4aQS9W0DvFtCHBXLg7ZN2XG9te8B_f3kG6j3w4Lyd_qPT89XVxd9yus-6NNifh6yJG11JLoW-XV1quM39can0Of8FXEmfqg</recordid><startdate>20160504</startdate><enddate>20160504</enddate><creator>Xiao, Yu-Lan</creator><creator>Min, Qiao-Qiao</creator><creator>Xu, Chang</creator><creator>Wang, Ruo-Wen</creator><creator>Zhang, Xingang</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20160504</creationdate><title>Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes</title><author>Xiao, Yu-Lan ; Min, Qiao-Qiao ; Xu, Chang ; Wang, Ruo-Wen ; Zhang, Xingang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4481-55ef25be89732086c7e8a0fad0a78140791905114b2172ca21336c2ed5e623a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>arenes</topic><topic>cross-coupling</topic><topic>fluorine</topic><topic>ligand design</topic><topic>Ligands</topic><topic>nickel</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xiao, Yu-Lan</creatorcontrib><creatorcontrib>Min, Qiao-Qiao</creatorcontrib><creatorcontrib>Xu, Chang</creatorcontrib><creatorcontrib>Wang, Ruo-Wen</creatorcontrib><creatorcontrib>Zhang, Xingang</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xiao, Yu-Lan</au><au>Min, Qiao-Qiao</au><au>Xu, Chang</au><au>Wang, Ruo-Wen</au><au>Zhang, Xingang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew. Chem. Int. Ed</addtitle><date>2016-05-04</date><risdate>2016</risdate><volume>55</volume><issue>19</issue><spage>5837</spage><epage>5841</epage><pages>5837-5841</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>A nickel‐catalyzed cross‐coupling between (hetero)arylborons and unactivated 1‐bromo‐1,1‐difluoroalkanes has been developed. The use of two ligands (a bidentate bipyridine‐based ligand, 4,4′‐ditBu‐bpy, and a monodentate pyridine‐based ligand, DMAP) offers a highly efficient nickel‐based catalytic system to prepare difluoroalkylated arenes which have important applications in medicinal chemistry.
Ligand combo: The title reaction requires the use of a combined (2+1) ligand system, that is, a combination of a bi‐ and monodentate ligand (4,4′‐ditBu‐bpy + DMAP). This system allows employment of a wide range of unactivated 1‐bromo‐1,1‐difluoroalkanes as coupling partners, thus providing a highly efficient method for applications in drug discovery and development. bpy=bipyridine, DMAP=4‐(N,N‐dimethylamino)pyridine.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27060704</pmid><doi>10.1002/anie.201601351</doi><tpages>5</tpages><edition>International ed. in English</edition></addata></record> |
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| subjects | arenes cross-coupling fluorine ligand design Ligands nickel |
| title | Nickel-Catalyzed Difluoroalkylation of (Hetero)Arylborons with Unactivated 1-Bromo-1,1-difluoroalkanes |
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