{"id":"https://openalex.org/W2033326208","doi":"https://doi.org/10.1002/047084289x.rt423","title":"Tris(triphenylphosphine)nickel(0)","display_name":"Tris(triphenylphosphine)nickel(0)","publication_year":2001,"publication_date":"2001-04-15","ids":{"openalex":"https://openalex.org/W2033326208","doi":"https://doi.org/10.1002/047084289x.rt423","mag":"2033326208"},"language":"en","primary_location":{"id":"doi:10.1002/047084289x.rt423","doi":"https://doi.org/10.1002/047084289x.rt423","is_oa":false,"landing_page_url":"https://doi.org/10.1002/047084289x.rt423","pdf_url":null,"source":{"id":"https://openalex.org/S4306464293","display_name":"Wiley eBooks","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"ebook platform"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Encyclopedia of Reagents for Organic Synthesis","raw_type":"reference-entry"},"volume":{"id":"https://openalex.org/W4212905075","display_name":"Encyclopedia of Reagents for Organic Synthesis"},"type":"reference-entry","indexed_in":["crossref"],"open_access":{"is_oa":false,"oa_status":"closed","oa_url":null,"any_repository_has_fulltext":false},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5060002438","display_name":"Paul A. Wender","orcid":"https://orcid.org/0000-0001-6319-2829","observed_orcids":["https://orcid.org/0000-0001-6319-2829"]},"institutions":[{"id":"https://openalex.org/I97018004","display_name":"Stanford University","ror":"https://ror.org/00f54p054","country_code":"US","type":"education","lineage":["https://openalex.org/I97018004"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Paul A. Wender","raw_affiliation_strings":["Stanford University, CA, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Stanford University, CA, USA","institution_ids":["https://openalex.org/I97018004"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5019890056","display_name":"Thomas E. Smith","orcid":"https://orcid.org/0000-0002-4031-7753","observed_orcids":["https://orcid.org/0000-0002-4031-7753"]},"institutions":[{"id":"https://openalex.org/I97018004","display_name":"Stanford University","ror":"https://ror.org/00f54p054","country_code":"US","type":"education","lineage":["https://openalex.org/I97018004"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Thomas E. Smith","raw_affiliation_strings":["Stanford University, CA, USA"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Stanford University, CA, USA","institution_ids":["https://openalex.org/I97018004"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":1,"corresponding_author_ids":[],"corresponding_institution_ids":["https://openalex.org/I97018004"],"apc_list":null,"apc_paid":null,"fwci":null,"has_fulltext":false,"cited_by_count":0,"citation_normalized_percentile":null,"cited_by_percentile_year":null,"biblio":{"volume":null,"issue":null,"first_page":null,"last_page":null},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.7588000297546387,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},"topics":[{"id":"https://openalex.org/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.7588000297546387,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T10092","display_name":"Organometallic Complex Synthesis and Catalysis","score":0.22310000658035278,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}},{"id":"https://openalex.org/T13239","display_name":"Phosphorus compounds and reactions","score":0.006599999964237213,"subfield":{"id":"https://openalex.org/subfields/1605","display_name":"Organic Chemistry"},"field":{"id":"https://openalex.org/fields/16","display_name":"Chemistry"},"domain":{"id":"https://openalex.org/domains/3","display_name":"Physical Sciences"}}],"keywords":[{"id":"https://openalex.org/keywords/aryl-halide-coupling","display_name":"aryl halide coupling","score":0.7379999756813049},{"id":"https://openalex.org/keywords/zinc-dust","display_name":"zinc dust","score":0.5649999976158142},{"id":"https://openalex.org/keywords/triphenylphosphine","display_name":"triphenylphosphine","score":0.902999997138977},{"id":"https://openalex.org/keywords/reagent-preparation","display_name":"reagent preparation","score":0.6499999761581421},{"id":"https://openalex.org/keywords/reagent-storage-and-handling","display_name":"reagent handling and storage","score":0.6510000228881836}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.7748852968215942},{"id":"https://openalex.org/C2778142098","wikidata":"https://www.wikidata.org/wiki/Q15779","display_name":"Toluene","level":2,"score":0.6491680145263672},{"id":"https://openalex.org/C2777247709","wikidata":"https://www.wikidata.org/wiki/Q115493","display_name":"Triphenylphosphine","level":3,"score":0.6467341184616089},{"id":"https://openalex.org/C504270822","wikidata":"https://www.wikidata.org/wiki/Q744","display_name":"Nickel","level":2,"score":0.6425787806510925},{"id":"https://openalex.org/C187714232","wikidata":"https://www.wikidata.org/wiki/Q2745207","display_name":"Anhydrous","level":2,"score":0.5926792621612549},{"id":"https://openalex.org/C535196362","wikidata":"https://www.wikidata.org/wiki/Q758","display_name":"Zinc","level":2,"score":0.5703523755073547},{"id":"https://openalex.org/C2781076698","wikidata":"https://www.wikidata.org/wiki/Q718074","display_name":"Aryl","level":3,"score":0.5131860375404358},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.5065640211105347},{"id":"https://openalex.org/C2780471494","wikidata":"https://www.wikidata.org/wiki/Q146505","display_name":"Solvent","level":2,"score":0.4844079613685608},{"id":"https://openalex.org/C155574463","wikidata":"https://www.wikidata.org/wiki/Q170731","display_name":"Solubility","level":2,"score":0.4523884952068329},{"id":"https://openalex.org/C171560689","wikidata":"https://www.wikidata.org/wiki/Q193086","display_name":"Halide","level":2,"score":0.42550987005233765},{"id":"https://openalex.org/C179104552","wikidata":"https://www.wikidata.org/wiki/Q11165","display_name":"Inorganic chemistry","level":1,"score":0.418569952249527},{"id":"https://openalex.org/C13965031","wikidata":"https://www.wikidata.org/wiki/Q243545","display_name":"Nuclear chemistry","level":1,"score":0.41353729367256165},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.2633365988731384},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.1999986171722412},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.1568981409072876}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.1002/047084289x.rt423","doi":"https://doi.org/10.1002/047084289x.rt423","is_oa":false,"landing_page_url":"https://doi.org/10.1002/047084289x.rt423","pdf_url":null,"source":{"id":"https://openalex.org/S4306464293","display_name":"Wiley eBooks","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/P4310320595","host_organization_name":"Wiley","host_organization_lineage":["https://openalex.org/P4310320595"],"host_organization_lineage_names":["Wiley"],"type":"ebook platform"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Encyclopedia of Reagents for Organic Synthesis","raw_type":"reference-entry"}],"best_oa_location":null,"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":false,"pdf":false},"content_urls":null,"referenced_works_count":34,"referenced_works":["https://openalex.org/W75320704","https://openalex.org/W130169337","https://openalex.org/W642390697","https://openalex.org/W1964015583","https://openalex.org/W1973723982","https://openalex.org/W1977119373","https://openalex.org/W1977380906","https://openalex.org/W1978335998","https://openalex.org/W1982298201","https://openalex.org/W1988191526","https://openalex.org/W1992639294","https://openalex.org/W1992654060","https://openalex.org/W2001492751","https://openalex.org/W2010039630","https://openalex.org/W2012470083","https://openalex.org/W2017719730","https://openalex.org/W2022102300","https://openalex.org/W2023243840","https://openalex.org/W2024208184","https://openalex.org/W2025852063","https://openalex.org/W2034058525","https://openalex.org/W2035872670","https://openalex.org/W2055779607","https://openalex.org/W2058709897","https://openalex.org/W2072761165","https://openalex.org/W2081264898","https://openalex.org/W2086066634","https://openalex.org/W2128551913","https://openalex.org/W2337547816","https://openalex.org/W2587564330","https://openalex.org/W2942292616","https://openalex.org/W2950096555","https://openalex.org/W2951887129","https://openalex.org/W2952619544"],"related_works":["https://openalex.org/W2125783476","https://openalex.org/W4233042273","https://openalex.org/W1811567863","https://openalex.org/W1547626017","https://openalex.org/W2098197860","https://openalex.org/W2059748689","https://openalex.org/W1594277599","https://openalex.org/W2152259805","https://openalex.org/W1853722120","https://openalex.org/W2322394715"],"abstract_inverted_index":{"[25136-46-3]":[0],"C54H45NiP3":[1],"(MW":[2],"845.59)":[3],"InChI":[4],"=":[5,8],"1S/3C18H15P.Ni/c3*1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;/h3*1-15H;":[6],"InChIKey":[7],"VGZIOHINNQGTOU-UHFFFAOYSA-N":[9],"(a":[10],"source":[11],"of":[12,18,25,29,47,67,76,87,92,103,118,130,146,180],"nickel(0)":[13],"useful":[14],"for":[15,94],"the":[16,61,65,74,109,120,127,144,167,174],"coupling":[17],"aryl,":[19],"alkenyl,":[20],"and":[21,57,108,148,171,187],"allyl":[22],"halides;2":[23],"oligomerization":[24,28],"strained":[26],"alkenes;3":[27],"allenes4)":[30],"Physical":[31],"Data:":[32],"mp":[33],"124\u2013126":[34],"\u00b0C":[35],"(N2).":[36],"Solubility:":[37],"sol":[38],"toluene,":[39],"benzene,":[40],"DMF,":[41],"DMA,":[42],"Et2O,":[43],"THF,":[44],"HMPA.":[45],"Analysis":[46],"Reagent":[48],"Purity:":[49],"1H":[50],"NMR":[51],"\u03b4":[52],"7.37":[53],"(o-H),":[54],"6.96":[55],"(m-":[56],"p-H).5":[58],"Preparative":[59],"Methods:":[60],"standard":[62],"preparation":[63,181],"involves":[64],"reduction":[66],"Nickel(II)":[68],"Chloride":[69],"with":[70,84],"Zinc":[71],"dust":[72,105],"in":[73,89,126,164],"presence":[75],"Triphenylphosphine.":[77],"Anhydrous":[78],"NiCl2":[79],"(2.6":[80],"g)":[81],"was":[82,106,111,124],"refluxed":[83],"21":[85],"g":[86,102],"PPh3":[88],"300":[90],"mL":[91],"acetonitrile":[93],"1":[95],"h.":[96],"After":[97,116],"cooling":[98],"to":[99,152],"rt,":[100],"2.0":[101],"zinc":[104],"added":[107],"mixture":[110],"stirred":[112],"under":[113,150],"nitrogen":[114],"overnight.":[115],"removal":[117],"solvent,":[119],"resulting":[121],"red":[122],"solid":[123],"dissolved":[125],"minimum":[128],"volume":[129],"hot":[131,140],"toluene":[132],"(60":[133],"\u00b0C),":[134],"removed":[135],"from":[136,166],"insoluble":[137],"impurities":[138],"by":[139,143],"filtration,":[141],"precipitated":[142],"addition":[145],"hexane,":[147],"dried":[149],"vacuum":[151],"give":[153],"a":[154],"reddish-brown":[155],"powder.5":[156],"This":[157],"precipitation":[158],"has":[159],"also":[160],"been":[161,183],"carried":[162],"out":[163],"situ":[165],"same":[168],"starting":[169],"materials":[170],"is":[172],"currently":[173],"favored":[175],"procedure.2":[176],"Several":[177],"other":[178],"methods":[179],"have":[182],"described.6":[184],"Handling,":[185],"Storage,":[186],"Precautions:":[188],"highly":[189],"oxygen":[190],"sensitive;":[191],"special":[192],"inert-atmosphere":[193],"techniques":[194],"must":[195],"be":[196,199],"used.7":[197],"Should":[198],"stored":[200],"at":[201],"0":[202],"\u00b0C.":[203]},"counts_by_year":[],"updated_date":"2026-11-05T12:25:35.769452","created_date":"2016-06-24T00:00:00"}
