Redox‐Active Ligand‐Assisted Two‐Electron Oxidative Addition to Gallium(II)

The reaction of digallane (dpp‐bian)Ga−Ga(dpp‐bian) (2) (dpp‐bian=1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene) with allyl chloride (AllCl) proceeded by a two‐electron oxidative addition to afford paramagnetic complexes (dpp‐bian)Ga(η1‐All)Cl (3) and (dpp‐bian)(Cl)Ga−Ga(Cl)(dpp‐bian) (4). Treat...

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Veröffentlicht in:Chemistry : a European journal 2018-02, Vol.24 (8), p.1877-1889
Hauptverfasser: Fedushkin, Igor L., Dodonov, Vladimir A., Skatova, Alexandra A., Sokolov, Vladimir G., Piskunov, Alexander V., Fukin, Georgii K.
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container_end_page 1889
container_issue 8
container_start_page 1877
container_title Chemistry : a European journal
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creator Fedushkin, Igor L.
Dodonov, Vladimir A.
Skatova, Alexandra A.
Sokolov, Vladimir G.
Piskunov, Alexander V.
Fukin, Georgii K.
description The reaction of digallane (dpp‐bian)Ga−Ga(dpp‐bian) (2) (dpp‐bian=1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene) with allyl chloride (AllCl) proceeded by a two‐electron oxidative addition to afford paramagnetic complexes (dpp‐bian)Ga(η1‐All)Cl (3) and (dpp‐bian)(Cl)Ga−Ga(Cl)(dpp‐bian) (4). Treatment of complex 4 with pyridine induced an intramolecular redox process, which resulted in the diamagnetic complex (dpp‐bian)Ga(Py)Cl (5). In reaction with allyl bromide, complex 2 gave metal‐ and ligand‐centered addition products (dpp‐bian)Ga(η1‐All)Br (6) and (dpp‐bian‐All)(Br)Ga−Ga(Br)(dpp‐bian‐All) (7). The reaction of digallane 2 with Ph3SnNCO afforded (dpp‐bian)Ga(SnPh3)2 (8) and (dpp‐bian)(NCO)Ga−Ga(NCO)(dpp‐bian) (9). Treatment of GaCl3 with (dpp‐bian)Na in diethyl ether resulted in the formation of (dpp‐bian)GaCl2 (10). Diorganylgallium derivatives (dpp‐bian)GaR2 (R=Ph, 11; tBu, 14; Me, 15; Bn, 16) and (dpp‐bian)Ga(η1‐All)R (R=nBu, 12; Cp, 13) were synthesized from complexes 3, 10, Bn2GaCl, or tBu2GaCl by salt metathesis. The salt elimination reaction between (dpp‐bian)GaI2 (17) and tBuLi was accompanied by reduction of both the metal and the dpp‐bian ligand, which resulted in digallane 2 as the final product. Similarly, the reaction of complex 10 with MentMgCl (Ment=menthyl) proceeded with reduction of the dpp‐bian ligand to give the diamagnetic complex [(dpp‐bian)GaCl2][Mg2Cl3(THF)6] (18). Compounds 11, 12, 13, 15, and 16 were thermally robust, whereas compound 14 decomposed when heated at reflux in toluene to give complex (dpp‐bian‐tBu)GatBu2 (19). Both complexes 7 and 19 contain R‐substituted dpp‐bian ligand: in the former compound the allyl group was attached to the imino‐carbon atom, whereas in complex 19, the tBu group was situated on the naphthalene ring. Crystal structures of complexes 3, 8, 9, 10, 13, 14, 18, and 19 were determined by single‐crystal X‐ray analysis. The presence of dpp‐bian radical anions in 3, 6, 8, and 10–16 was determined by ESR spectroscopy. Gallium complexes: Redox‐active catalysts can substantially expand the reactivity of metal complexes, which can enable possible applications into catalysis. They are commonly incorporated into transition‐metal complexes; however, this paper reports the oxidative addition of organic substrates to a gallium complex of redox‐active 1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene (see scheme).
doi_str_mv 10.1002/chem.201704128
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Treatment of complex 4 with pyridine induced an intramolecular redox process, which resulted in the diamagnetic complex (dpp‐bian)Ga(Py)Cl (5). In reaction with allyl bromide, complex 2 gave metal‐ and ligand‐centered addition products (dpp‐bian)Ga(η1‐All)Br (6) and (dpp‐bian‐All)(Br)Ga−Ga(Br)(dpp‐bian‐All) (7). The reaction of digallane 2 with Ph3SnNCO afforded (dpp‐bian)Ga(SnPh3)2 (8) and (dpp‐bian)(NCO)Ga−Ga(NCO)(dpp‐bian) (9). Treatment of GaCl3 with (dpp‐bian)Na in diethyl ether resulted in the formation of (dpp‐bian)GaCl2 (10). Diorganylgallium derivatives (dpp‐bian)GaR2 (R=Ph, 11; tBu, 14; Me, 15; Bn, 16) and (dpp‐bian)Ga(η1‐All)R (R=nBu, 12; Cp, 13) were synthesized from complexes 3, 10, Bn2GaCl, or tBu2GaCl by salt metathesis. The salt elimination reaction between (dpp‐bian)GaI2 (17) and tBuLi was accompanied by reduction of both the metal and the dpp‐bian ligand, which resulted in digallane 2 as the final product. Similarly, the reaction of complex 10 with MentMgCl (Ment=menthyl) proceeded with reduction of the dpp‐bian ligand to give the diamagnetic complex [(dpp‐bian)GaCl2][Mg2Cl3(THF)6] (18). Compounds 11, 12, 13, 15, and 16 were thermally robust, whereas compound 14 decomposed when heated at reflux in toluene to give complex (dpp‐bian‐tBu)GatBu2 (19). Both complexes 7 and 19 contain R‐substituted dpp‐bian ligand: in the former compound the allyl group was attached to the imino‐carbon atom, whereas in complex 19, the tBu group was situated on the naphthalene ring. Crystal structures of complexes 3, 8, 9, 10, 13, 14, 18, and 19 were determined by single‐crystal X‐ray analysis. The presence of dpp‐bian radical anions in 3, 6, 8, and 10–16 was determined by ESR spectroscopy. Gallium complexes: Redox‐active catalysts can substantially expand the reactivity of metal complexes, which can enable possible applications into catalysis. They are commonly incorporated into transition‐metal complexes; however, this paper reports the oxidative addition of organic substrates to a gallium complex of redox‐active 1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene (see scheme).</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201704128</identifier><identifier>PMID: 29125198</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Acenaphthene ; Allyl chloride ; Anions ; Chemistry ; Coordination compounds ; Crystal structure ; Diamagnetism ; Diethyl ether ; ESR spectroscopy ; Gallium ; Ligands ; Metals ; Metathesis ; Naphthalene ; oxidative addition ; Pyridines ; redox-active ligands ; Reduction (metal working) ; Salts ; Single crystals ; Spectroscopy ; Toluene ; X ray analysis ; X-ray diffraction</subject><ispartof>Chemistry : a European journal, 2018-02, Vol.24 (8), p.1877-1889</ispartof><rights>2018 Wiley‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><rights>2018 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim.</rights><rights>2018 Wiley-VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4768-7913cc36c46ba10c2441d0372c1c13b5485e4ff2b502ffaa6eb290a005a8ef63</citedby><cites>FETCH-LOGICAL-c4768-7913cc36c46ba10c2441d0372c1c13b5485e4ff2b502ffaa6eb290a005a8ef63</cites><orcidid>0000-0003-2664-2266</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201704128$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201704128$$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/29125198$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fedushkin, Igor L.</creatorcontrib><creatorcontrib>Dodonov, Vladimir A.</creatorcontrib><creatorcontrib>Skatova, Alexandra A.</creatorcontrib><creatorcontrib>Sokolov, Vladimir G.</creatorcontrib><creatorcontrib>Piskunov, Alexander V.</creatorcontrib><creatorcontrib>Fukin, Georgii K.</creatorcontrib><title>Redox‐Active Ligand‐Assisted Two‐Electron Oxidative Addition to Gallium(II)</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>The reaction of digallane (dpp‐bian)Ga−Ga(dpp‐bian) (2) (dpp‐bian=1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene) with allyl chloride (AllCl) proceeded by a two‐electron oxidative addition to afford paramagnetic complexes (dpp‐bian)Ga(η1‐All)Cl (3) and (dpp‐bian)(Cl)Ga−Ga(Cl)(dpp‐bian) (4). Treatment of complex 4 with pyridine induced an intramolecular redox process, which resulted in the diamagnetic complex (dpp‐bian)Ga(Py)Cl (5). In reaction with allyl bromide, complex 2 gave metal‐ and ligand‐centered addition products (dpp‐bian)Ga(η1‐All)Br (6) and (dpp‐bian‐All)(Br)Ga−Ga(Br)(dpp‐bian‐All) (7). The reaction of digallane 2 with Ph3SnNCO afforded (dpp‐bian)Ga(SnPh3)2 (8) and (dpp‐bian)(NCO)Ga−Ga(NCO)(dpp‐bian) (9). Treatment of GaCl3 with (dpp‐bian)Na in diethyl ether resulted in the formation of (dpp‐bian)GaCl2 (10). Diorganylgallium derivatives (dpp‐bian)GaR2 (R=Ph, 11; tBu, 14; Me, 15; Bn, 16) and (dpp‐bian)Ga(η1‐All)R (R=nBu, 12; Cp, 13) were synthesized from complexes 3, 10, Bn2GaCl, or tBu2GaCl by salt metathesis. The salt elimination reaction between (dpp‐bian)GaI2 (17) and tBuLi was accompanied by reduction of both the metal and the dpp‐bian ligand, which resulted in digallane 2 as the final product. Similarly, the reaction of complex 10 with MentMgCl (Ment=menthyl) proceeded with reduction of the dpp‐bian ligand to give the diamagnetic complex [(dpp‐bian)GaCl2][Mg2Cl3(THF)6] (18). Compounds 11, 12, 13, 15, and 16 were thermally robust, whereas compound 14 decomposed when heated at reflux in toluene to give complex (dpp‐bian‐tBu)GatBu2 (19). Both complexes 7 and 19 contain R‐substituted dpp‐bian ligand: in the former compound the allyl group was attached to the imino‐carbon atom, whereas in complex 19, the tBu group was situated on the naphthalene ring. Crystal structures of complexes 3, 8, 9, 10, 13, 14, 18, and 19 were determined by single‐crystal X‐ray analysis. The presence of dpp‐bian radical anions in 3, 6, 8, and 10–16 was determined by ESR spectroscopy. Gallium complexes: Redox‐active catalysts can substantially expand the reactivity of metal complexes, which can enable possible applications into catalysis. They are commonly incorporated into transition‐metal complexes; however, this paper reports the oxidative addition of organic substrates to a gallium complex of redox‐active 1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene (see scheme).</description><subject>Acenaphthene</subject><subject>Allyl chloride</subject><subject>Anions</subject><subject>Chemistry</subject><subject>Coordination compounds</subject><subject>Crystal structure</subject><subject>Diamagnetism</subject><subject>Diethyl ether</subject><subject>ESR spectroscopy</subject><subject>Gallium</subject><subject>Ligands</subject><subject>Metals</subject><subject>Metathesis</subject><subject>Naphthalene</subject><subject>oxidative addition</subject><subject>Pyridines</subject><subject>redox-active ligands</subject><subject>Reduction (metal working)</subject><subject>Salts</subject><subject>Single crystals</subject><subject>Spectroscopy</subject><subject>Toluene</subject><subject>X ray analysis</subject><subject>X-ray diffraction</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqF0E1PwjAYB_DGaATRq0dD4gUPwz592dYjIQgkGKLhvnRdpyV70XUTuPkR_Ix-EosgJl7spXmaX_9p_whdAu4DxuRWPeu8TzAEmAEJj1AbOAGPBj4_Rm0sWOD5nIoWOrN2iTEWPqWnqEUEEA4ibKOHR52U68_3j4GqzZvuzsyTLJLtbK2xtU66i1XpxlGmVV2VRXe-Non8poMkMbVxR3XZHcssM03em05vztFJKjOrL_Z7By3uRovhxJvNx9PhYOYpFvihFwigSlFfMT-WgBVhDBJMA6JAAY05C7lmaUpijkmaSunrmAgsMeYy1KlPO6i3i32pytdG2zrKjVU6y2Shy8ZG4L5KAuaWo9d_6LJsqsI9zinBKAsAQqf6O6Wq0tpKp9FLZXJZbSLA0bbraNt1dOjaXbjaxzZxrpMD_ynXAbEDK5PpzT9x0XAyuv8N_wLdE4xB</recordid><startdate>20180206</startdate><enddate>20180206</enddate><creator>Fedushkin, Igor L.</creator><creator>Dodonov, Vladimir A.</creator><creator>Skatova, Alexandra A.</creator><creator>Sokolov, Vladimir G.</creator><creator>Piskunov, Alexander V.</creator><creator>Fukin, Georgii K.</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2664-2266</orcidid></search><sort><creationdate>20180206</creationdate><title>Redox‐Active Ligand‐Assisted Two‐Electron Oxidative Addition to Gallium(II)</title><author>Fedushkin, Igor L. ; Dodonov, Vladimir A. ; Skatova, Alexandra A. ; Sokolov, Vladimir G. ; Piskunov, Alexander V. ; Fukin, Georgii K.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4768-7913cc36c46ba10c2441d0372c1c13b5485e4ff2b502ffaa6eb290a005a8ef63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acenaphthene</topic><topic>Allyl chloride</topic><topic>Anions</topic><topic>Chemistry</topic><topic>Coordination compounds</topic><topic>Crystal structure</topic><topic>Diamagnetism</topic><topic>Diethyl ether</topic><topic>ESR spectroscopy</topic><topic>Gallium</topic><topic>Ligands</topic><topic>Metals</topic><topic>Metathesis</topic><topic>Naphthalene</topic><topic>oxidative addition</topic><topic>Pyridines</topic><topic>redox-active ligands</topic><topic>Reduction (metal working)</topic><topic>Salts</topic><topic>Single crystals</topic><topic>Spectroscopy</topic><topic>Toluene</topic><topic>X ray analysis</topic><topic>X-ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fedushkin, Igor L.</creatorcontrib><creatorcontrib>Dodonov, Vladimir A.</creatorcontrib><creatorcontrib>Skatova, Alexandra A.</creatorcontrib><creatorcontrib>Sokolov, Vladimir G.</creatorcontrib><creatorcontrib>Piskunov, Alexander V.</creatorcontrib><creatorcontrib>Fukin, Georgii K.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health &amp; Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fedushkin, Igor L.</au><au>Dodonov, Vladimir A.</au><au>Skatova, Alexandra A.</au><au>Sokolov, Vladimir G.</au><au>Piskunov, Alexander V.</au><au>Fukin, Georgii K.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Redox‐Active Ligand‐Assisted Two‐Electron Oxidative Addition to Gallium(II)</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2018-02-06</date><risdate>2018</risdate><volume>24</volume><issue>8</issue><spage>1877</spage><epage>1889</epage><pages>1877-1889</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>The reaction of digallane (dpp‐bian)Ga−Ga(dpp‐bian) (2) (dpp‐bian=1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene) with allyl chloride (AllCl) proceeded by a two‐electron oxidative addition to afford paramagnetic complexes (dpp‐bian)Ga(η1‐All)Cl (3) and (dpp‐bian)(Cl)Ga−Ga(Cl)(dpp‐bian) (4). Treatment of complex 4 with pyridine induced an intramolecular redox process, which resulted in the diamagnetic complex (dpp‐bian)Ga(Py)Cl (5). In reaction with allyl bromide, complex 2 gave metal‐ and ligand‐centered addition products (dpp‐bian)Ga(η1‐All)Br (6) and (dpp‐bian‐All)(Br)Ga−Ga(Br)(dpp‐bian‐All) (7). The reaction of digallane 2 with Ph3SnNCO afforded (dpp‐bian)Ga(SnPh3)2 (8) and (dpp‐bian)(NCO)Ga−Ga(NCO)(dpp‐bian) (9). Treatment of GaCl3 with (dpp‐bian)Na in diethyl ether resulted in the formation of (dpp‐bian)GaCl2 (10). Diorganylgallium derivatives (dpp‐bian)GaR2 (R=Ph, 11; tBu, 14; Me, 15; Bn, 16) and (dpp‐bian)Ga(η1‐All)R (R=nBu, 12; Cp, 13) were synthesized from complexes 3, 10, Bn2GaCl, or tBu2GaCl by salt metathesis. The salt elimination reaction between (dpp‐bian)GaI2 (17) and tBuLi was accompanied by reduction of both the metal and the dpp‐bian ligand, which resulted in digallane 2 as the final product. Similarly, the reaction of complex 10 with MentMgCl (Ment=menthyl) proceeded with reduction of the dpp‐bian ligand to give the diamagnetic complex [(dpp‐bian)GaCl2][Mg2Cl3(THF)6] (18). Compounds 11, 12, 13, 15, and 16 were thermally robust, whereas compound 14 decomposed when heated at reflux in toluene to give complex (dpp‐bian‐tBu)GatBu2 (19). Both complexes 7 and 19 contain R‐substituted dpp‐bian ligand: in the former compound the allyl group was attached to the imino‐carbon atom, whereas in complex 19, the tBu group was situated on the naphthalene ring. Crystal structures of complexes 3, 8, 9, 10, 13, 14, 18, and 19 were determined by single‐crystal X‐ray analysis. The presence of dpp‐bian radical anions in 3, 6, 8, and 10–16 was determined by ESR spectroscopy. Gallium complexes: Redox‐active catalysts can substantially expand the reactivity of metal complexes, which can enable possible applications into catalysis. They are commonly incorporated into transition‐metal complexes; however, this paper reports the oxidative addition of organic substrates to a gallium complex of redox‐active 1,2‐bis[(2,6‐diisopropylphenyl)imino]acenaphthene (see scheme).</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>29125198</pmid><doi>10.1002/chem.201704128</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0003-2664-2266</orcidid></addata></record>
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source Wiley Online Library Journals Frontfile Complete
subjects Acenaphthene
Allyl chloride
Anions
Chemistry
Coordination compounds
Crystal structure
Diamagnetism
Diethyl ether
ESR spectroscopy
Gallium
Ligands
Metals
Metathesis
Naphthalene
oxidative addition
Pyridines
redox-active ligands
Reduction (metal working)
Salts
Single crystals
Spectroscopy
Toluene
X ray analysis
X-ray diffraction
title Redox‐Active Ligand‐Assisted Two‐Electron Oxidative Addition to Gallium(II)
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