{"id":"https://openalex.org/W4243661986","doi":"https://doi.org/10.26434/chemrxiv.12378104","title":"Halogen\u2013Sodium Exchange Revisited","display_name":"Halogen\u2013Sodium Exchange Revisited","publication_year":2020,"publication_date":"2020-05-29","ids":{"openalex":"https://openalex.org/W4243661986","doi":"https://doi.org/10.26434/chemrxiv.12378104"},"language":"en","primary_location":{"id":"doi:10.26434/chemrxiv.12378104","doi":"https://doi.org/10.26434/chemrxiv.12378104","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.12378104","pdf_url":"https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/60c74bc5702a9bc24418b516/original/halogen-sodium-exchange-revisited.pdf","source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},"volume":null,"type":"preprint","is_traditional":true,"indexed_in":["crossref"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/60c74bc5702a9bc24418b516/original/halogen-sodium-exchange-revisited.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5015920204","display_name":"Sobi Asako","orcid":"https://orcid.org/0000-0003-4525-5317","observed_orcids":["https://orcid.org/0000-0003-4525-5317"]},"institutions":[{"id":"https://openalex.org/I4210100240","display_name":"RIKEN Center for Sustainable Resource Science","ror":"https://ror.org/010rf2m76","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210100240","https://openalex.org/I4210110652"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Sobi Asako","raw_affiliation_strings":["RIKEN Center for Sustainable Resource Science"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"RIKEN Center for Sustainable Resource Science","institution_ids":["https://openalex.org/I4210100240"]}]},{"author_position":"middle","author":{"id":null,"display_name":"Ikko Takahashi","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210100240","display_name":"RIKEN Center for Sustainable Resource Science","ror":"https://ror.org/010rf2m76","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210100240","https://openalex.org/I4210110652"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Ikko Takahashi","raw_affiliation_strings":["RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan","institution_ids":["https://openalex.org/I4210100240"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5110731747","display_name":"Hirotaka Nakajima","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I163770644","display_name":"Okayama University","ror":"https://ror.org/02pc6pc55","country_code":"JP","type":"education","lineage":["https://openalex.org/I163770644"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Hirotaka Nakajima","raw_affiliation_strings":["Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan","institution_ids":["https://openalex.org/I163770644"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5019911959","display_name":"Laurean Ilies","orcid":"https://orcid.org/0000-0002-0514-2740","observed_orcids":["https://orcid.org/0000-0002-0514-2740"]},"institutions":[{"id":"https://openalex.org/I4210100240","display_name":"RIKEN Center for Sustainable Resource Science","ror":"https://ror.org/010rf2m76","country_code":"JP","type":"facility","lineage":["https://openalex.org/I4210100240","https://openalex.org/I4210110652"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Laurean Ilies","raw_affiliation_strings":["RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"RIKEN Center for Sustainable Resource Science, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan","institution_ids":["https://openalex.org/I4210100240"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5021746646","display_name":"Kazuhiko Takai","orcid":"https://orcid.org/0000-0002-2572-0851","observed_orcids":["https://orcid.org/0000-0002-2572-0851"]},"institutions":[{"id":"https://openalex.org/I163770644","display_name":"Okayama University","ror":"https://ror.org/02pc6pc55","country_code":"JP","type":"education","lineage":["https://openalex.org/I163770644"]}],"countries":["JP"],"is_corresponding":false,"raw_author_name":"Kazuhiko Takai","raw_affiliation_strings":["Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan","institution_ids":["https://openalex.org/I163770644"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":null,"has_fulltext":true,"cited_by_count":1,"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/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.9980000257492065,"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/T12228","display_name":"Coordination Chemistry and Organometallics","score":0.9980000257492065,"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/T10548","display_name":"Catalytic Cross-Coupling Reactions","score":0.0008999999845400453,"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/T11441","display_name":"Organoboron and organosilicon chemistry","score":0.00019999999494757503,"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/organosodium-compounds","display_name":"organosodium compounds","score":0.9559999704360962},{"id":"https://openalex.org/keywords/sodium-dispersion","display_name":"sodium dispersion","score":0.9089999794960022},{"id":"https://openalex.org/keywords/beta-hydride-elimination","display_name":"\u03b2-hydride elimination","score":0.8569999933242798},{"id":"https://openalex.org/keywords/sustainable-synthesis","display_name":"sustainable synthesis","score":0.6259999871253967}],"concepts":[{"id":"https://openalex.org/C46062151","wikidata":"https://www.wikidata.org/wiki/Q19605","display_name":"Halogen","level":3,"score":0.8360046148300171},{"id":"https://openalex.org/C537181965","wikidata":"https://www.wikidata.org/wiki/Q658","display_name":"Sodium","level":2,"score":0.6859897375106812},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6661252975463867},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.5315361618995667},{"id":"https://openalex.org/C198091228","wikidata":"https://www.wikidata.org/wiki/Q19557","display_name":"Alkali metal","level":2,"score":0.5202237963676453},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.4806745946407318},{"id":"https://openalex.org/C535685238","wikidata":"https://www.wikidata.org/wiki/Q1153832","display_name":"Organic synthesis","level":3,"score":0.44718798995018005},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3516654372215271},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.26590263843536377},{"id":"https://openalex.org/C2780263894","wikidata":"https://www.wikidata.org/wiki/Q335268","display_name":"Alkyl","level":2,"score":0.06081342697143555}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.26434/chemrxiv.12378104","doi":"https://doi.org/10.26434/chemrxiv.12378104","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.12378104","pdf_url":"https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/60c74bc5702a9bc24418b516/original/halogen-sodium-exchange-revisited.pdf","source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"}],"best_oa_location":{"id":"doi:10.26434/chemrxiv.12378104","doi":"https://doi.org/10.26434/chemrxiv.12378104","is_oa":true,"landing_page_url":"https://doi.org/10.26434/chemrxiv.12378104","pdf_url":"https://chemrxiv.org/engage/api-gateway/chemrxiv/assets/orp/resource/item/60c74bc5702a9bc24418b516/original/halogen-sodium-exchange-revisited.pdf","source":{"id":"https://openalex.org/S4393918830","display_name":"ChemRxiv","issn_l":"2573-2293","issn":["2573-2293"],"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":null,"host_organization_name":null,"host_organization_lineage":[],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc-nd","license_id":"https://openalex.org/licenses/cc-by-nc-nd","version":"submittedVersion","is_accepted":false,"is_published":false,"raw_source_name":null,"raw_type":"posted-content"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[{"id":"https://openalex.org/F4320335125","display_name":"RIKEN","ror":"https://ror.org/01sjwvz98"}],"has_content":{"grobid_xml":true,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4243661986.pdf","grobid_xml":"https://content.openalex.org/works/W4243661986.grobid-xml"},"referenced_works_count":19,"referenced_works":["https://openalex.org/W1524358546","https://openalex.org/W1543800107","https://openalex.org/W1997376154","https://openalex.org/W2013760130","https://openalex.org/W2049297122","https://openalex.org/W2074673201","https://openalex.org/W2169269629","https://openalex.org/W2171942425","https://openalex.org/W2316122583","https://openalex.org/W2321571637","https://openalex.org/W2334118459","https://openalex.org/W2488653050","https://openalex.org/W2810186443","https://openalex.org/W2921529578","https://openalex.org/W2936537614","https://openalex.org/W2952248941","https://openalex.org/W2955480939","https://openalex.org/W3010001157","https://openalex.org/W4241426265"],"related_works":["https://openalex.org/W3164968939","https://openalex.org/W3169997414","https://openalex.org/W4417112909","https://openalex.org/W3154590293","https://openalex.org/W4387409314","https://openalex.org/W392520413","https://openalex.org/W4283215371","https://openalex.org/W2012449633","https://openalex.org/W1985096050","https://openalex.org/W4400243052"],"abstract_inverted_index":{"Sodium":[0],"is":[1,36,81],"the":[2,40,48,82,122,128,136,146,153],"most":[3],"abundant":[4],"alkali":[5],"metal":[6],"on":[7],"Earth.":[8],"Despite":[9],"being":[10],"an":[11,99],"attractive":[12],"choice":[13],"for":[14,47,135],"sustainable":[15,149],"synthesis,":[16,142],"organosodium":[17,51,139],"compounds":[18],"are":[19],"rarely":[20],"used":[21],"in":[22,93,140],"organic":[23,141],"synthesis":[24],"and":[25,44,67,98,111,114,125],"have":[26],"been":[27],"overshadowed":[28],"to":[29,39,60,145],"date":[30],"by":[31,75,151],"organolithium":[32,156],"compounds.":[33,52],"This":[34],"situation":[35],"largely":[37],"due":[38],"lack":[41],"of":[42,50,65,71,84,127,138,148],"convenient":[43],"efficient":[45,116],"methods":[46],"preparation":[49],"We":[53,119],"report":[54],"herein":[55],"a":[56,62,85,89],"halogen\u2013sodium":[57],"exchange":[58],"method":[59,130],"prepare":[61],"large":[63],"variety":[64],"(hetero)aryl-":[66],"alkenylsodium":[68],"compounds,":[69],"many":[70],"them":[72],"previously":[73],"inaccessible":[74],"other":[76],"methods.":[77],"The":[78],"key":[79],"discovery":[80],"use":[83,137],"bulky":[86],"alkylsodium":[87],"lacking":[88],"\u03b2-hydrogen,":[90],"readily":[91],"prepared":[92],"situ":[94],"from":[95],"neopentyl":[96],"chloride":[97],"easy-to-handle":[100],"sodium":[101],"dispersion,":[102],"which":[103],"retards":[104],"undesired":[105],"reactions":[106],"such":[107],"as":[108],"Wurtz\u2013Fittig":[109],"coupling":[110],"\u03b2-hydrogen":[112],"elimination,":[113],"enables":[115],"halogen-sodium":[117],"exchange.":[118],"believe":[120],"that":[121],"efficiency,":[123],"generality,":[124],"convenience":[126],"present":[129],"will":[131],"open":[132],"new":[133],"horizons":[134],"ultimately":[143],"contributing":[144],"development":[147],"chemistry":[150],"replacing":[152],"currently":[154],"dominant":[155],"reagents.":[157]},"counts_by_year":[{"year":2025,"cited_by_count":1}],"updated_date":"2026-11-09T13:22:03.289127","created_date":"2022-05-12T00:00:00"}
