{"id":"https://openalex.org/W4415495458","doi":"https://doi.org/10.21203/rs.3.rs-7819613/v1","title":"Amide Synthesis via Molecular Shuffling of Carboxylic Acids","display_name":"Amide Synthesis via Molecular Shuffling of Carboxylic Acids","publication_year":2025,"publication_date":"2025-10-24","ids":{"openalex":"https://openalex.org/W4415495458","doi":"https://doi.org/10.21203/rs.3.rs-7819613/v1"},"language":"en","primary_location":{"id":"doi:10.21203/rs.3.rs-7819613/v1","doi":"https://doi.org/10.21203/rs.3.rs-7819613/v1","is_oa":true,"landing_page_url":"https://doi.org/10.21203/rs.3.rs-7819613/v1","pdf_url":"https://www.researchsquare.com/article/rs-7819613/latest.pdf","source":{"id":"https://openalex.org/S4306525896","display_name":"Research Square","issn_l":null,"issn":null,"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","license_id":"https://openalex.org/licenses/cc-by","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"Research Square","raw_type":"posted-content"},"volume":null,"type":"preprint","indexed_in":["crossref"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://www.researchsquare.com/article/rs-7819613/latest.pdf","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5073616464","display_name":"Tieqiao Chen","orcid":"https://orcid.org/0000-0002-9787-9538","observed_orcids":["https://orcid.org/0000-0002-9787-9538"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Tieqiao Chen","raw_affiliation_strings":["Hainan University"],"raw_orcid":"https://orcid.org/0000-0002-9787-9538","affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100398939","display_name":"Chenglong Li","orcid":"https://orcid.org/0000-0003-2523-6151","observed_orcids":["https://orcid.org/0000-0003-2523-6151"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Chenglong Li","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5065058251","display_name":"Qihang Tan","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Qihang Tan","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5078727121","display_name":"Qihong Wu","orcid":"https://orcid.org/0000-0002-1296-8225","observed_orcids":["https://orcid.org/0000-0002-1296-8225"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Qiang Wu","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5102324267","display_name":"Yun Zhi Fu","orcid":"https://orcid.org/0000-0001-9975-2007","observed_orcids":["https://orcid.org/0000-0001-9975-2007"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Yun Fu","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100724873","display_name":"Yongmei Wang","orcid":"https://orcid.org/0000-0002-7418-9489","observed_orcids":["https://orcid.org/0000-0002-7418-9489","https://orcid.org/0000-0002-1328-9574"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Yongmei Wang","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5101506434","display_name":"Bin Song","orcid":"https://orcid.org/0009-0002-2314-0172","observed_orcids":["https://orcid.org/0009-0002-2314-0172"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Bin Song","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5068352543","display_name":"Tianzeng Huang","orcid":"https://orcid.org/0000-0002-1568-0817","observed_orcids":["https://orcid.org/0000-0002-1568-0817"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Tianzeng Huang","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5100348289","display_name":"Long Liu","orcid":"https://orcid.org/0000-0002-6472-5057","observed_orcids":["https://orcid.org/0000-0002-6472-5057"]},"institutions":[{"id":"https://openalex.org/I20942203","display_name":"Hainan University","ror":"https://ror.org/03q648j11","country_code":"CN","type":"education","lineage":["https://openalex.org/I20942203"]}],"countries":["CN"],"is_corresponding":false,"raw_author_name":"Long Liu","raw_affiliation_strings":["Hainan University"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Hainan University","institution_ids":["https://openalex.org/I20942203"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5068601986","display_name":"Michal Szostak","orcid":"https://orcid.org/0000-0002-9650-9690","observed_orcids":["https://orcid.org/0000-0002-9650-9690"]},"institutions":[{"id":"https://openalex.org/I102322142","display_name":"Rutgers, The State University of New Jersey","ror":"https://ror.org/05vt9qd57","country_code":"US","type":"education","lineage":["https://openalex.org/I102322142"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Michal Szostak","raw_affiliation_strings":["Rutgers University"],"raw_orcid":"https://orcid.org/0000-0002-9650-9690","affiliations":[{"raw_affiliation_string":"Rutgers University","institution_ids":["https://openalex.org/I102322142"]}]}],"institutions":[],"countries_distinct_count":2,"institutions_distinct_count":2,"corresponding_author_ids":[],"corresponding_institution_ids":[],"apc_list":null,"apc_paid":null,"fwci":null,"has_fulltext":true,"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":0.8398000001907349,"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":0.8398000001907349,"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":0.0835999995470047,"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/T10354","display_name":"Catalytic C\u2013H Functionalization Methods","score":0.019600000232458115,"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/amide-synthesis","display_name":"amide synthesis","score":0.9810000061988831},{"id":"https://openalex.org/keywords/carboxylic-acids","display_name":"carboxylic acids","score":0.7599999904632568},{"id":"https://openalex.org/keywords/oxidative-addition","display_name":"oxidative addition","score":0.5720000267028809},{"id":"https://openalex.org/keywords/palladium-catalysis","display_name":"palladium catalysis","score":0.8399999737739563},{"id":"https://openalex.org/keywords/decarbonylation","display_name":"decarbonylation","score":0.8920000195503235},{"id":"https://openalex.org/keywords/alkene-insertion","display_name":"alkene insertion","score":0.8560000061988831},{"id":"https://openalex.org/keywords/reductive-elimination","display_name":"reductive elimination","score":0.9190000295639038},{"id":"https://openalex.org/keywords/late-stage-functionalization","display_name":"late-stage functionalization","score":0.800000011920929}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.8137999773025513},{"id":"https://openalex.org/C2778439535","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Amide","level":2,"score":0.739300012588501},{"id":"https://openalex.org/C2776254738","wikidata":"https://www.wikidata.org/wiki/Q81406","display_name":"Alkene","level":3,"score":0.6315000057220459},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6071000099182129},{"id":"https://openalex.org/C132190689","wikidata":"https://www.wikidata.org/wiki/Q15197274","display_name":"Decarbonylation","level":3,"score":0.5906000137329102},{"id":"https://openalex.org/C2777332933","wikidata":"https://www.wikidata.org/wiki/Q170409","display_name":"Functional group","level":3,"score":0.5871000289916992},{"id":"https://openalex.org/C2779074116","wikidata":"https://www.wikidata.org/wiki/Q134856","display_name":"Carboxylic acid","level":2,"score":0.5289000272750854},{"id":"https://openalex.org/C31684184","wikidata":"https://www.wikidata.org/wiki/Q33293","display_name":"Peptide bond","level":3,"score":0.46549999713897705},{"id":"https://openalex.org/C114373084","wikidata":"https://www.wikidata.org/wiki/Q273499","display_name":"Chemical synthesis","level":3,"score":0.45080000162124634},{"id":"https://openalex.org/C71866858","wikidata":"https://www.wikidata.org/wiki/Q902756","display_name":"Negishi coupling","level":3,"score":0.4050000011920929},{"id":"https://openalex.org/C535685238","wikidata":"https://www.wikidata.org/wiki/Q1153832","display_name":"Organic synthesis","level":3,"score":0.39969998598098755},{"id":"https://openalex.org/C2778844314","wikidata":"https://www.wikidata.org/wiki/Q191700","display_name":"Benzoic acid","level":2,"score":0.3901999890804291},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.3840000033378601},{"id":"https://openalex.org/C116569031","wikidata":"https://www.wikidata.org/wiki/Q899107","display_name":"Ligand (biochemistry)","level":3,"score":0.36980000138282776},{"id":"https://openalex.org/C131779359","wikidata":"https://www.wikidata.org/wiki/Q471875","display_name":"Amine gas treating","level":2,"score":0.3587000072002411},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3522999882698059},{"id":"https://openalex.org/C2779746882","wikidata":"https://www.wikidata.org/wiki/Q898525","display_name":"Protecting group","level":3,"score":0.3336000144481659},{"id":"https://openalex.org/C71240020","wikidata":"https://www.wikidata.org/wiki/Q186011","display_name":"Stereochemistry","level":1,"score":0.3239000141620636},{"id":"https://openalex.org/C2778815869","wikidata":"https://www.wikidata.org/wiki/Q25325213","display_name":"Reductive elimination","level":3,"score":0.31049999594688416},{"id":"https://openalex.org/C207245611","wikidata":"https://www.wikidata.org/wiki/Q910058","display_name":"Condensation reaction","level":3,"score":0.2939999997615814},{"id":"https://openalex.org/C2778327999","wikidata":"https://www.wikidata.org/wiki/Q188777","display_name":"Carboxamide","level":2,"score":0.2809000015258789},{"id":"https://openalex.org/C108797602","wikidata":"https://www.wikidata.org/wiki/Q1059835","display_name":"Single bond","level":3,"score":0.2718000113964081},{"id":"https://openalex.org/C38489247","wikidata":"https://www.wikidata.org/wiki/Q413110","display_name":"Nitrene","level":3,"score":0.26899999380111694},{"id":"https://openalex.org/C2776378156","wikidata":"https://www.wikidata.org/wiki/Q408018","display_name":"Enamine","level":3,"score":0.2655999958515167},{"id":"https://openalex.org/C2985598853","wikidata":"https://www.wikidata.org/wiki/Q644785","display_name":"Formal synthesis","level":2,"score":0.2648000121116638},{"id":"https://openalex.org/C68381374","wikidata":"https://www.wikidata.org/wiki/Q258652","display_name":"Double bond","level":2,"score":0.262800008058548},{"id":"https://openalex.org/C193557335","wikidata":"https://www.wikidata.org/wiki/Q61424","display_name":"Acylation","level":3,"score":0.2526000142097473}],"mesh":[],"locations_count":1,"locations":[{"id":"doi:10.21203/rs.3.rs-7819613/v1","doi":"https://doi.org/10.21203/rs.3.rs-7819613/v1","is_oa":true,"landing_page_url":"https://doi.org/10.21203/rs.3.rs-7819613/v1","pdf_url":"https://www.researchsquare.com/article/rs-7819613/latest.pdf","source":{"id":"https://openalex.org/S4306525896","display_name":"Research Square","issn_l":null,"issn":null,"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","license_id":"https://openalex.org/licenses/cc-by","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"Research Square","raw_type":"posted-content"}],"best_oa_location":{"id":"doi:10.21203/rs.3.rs-7819613/v1","doi":"https://doi.org/10.21203/rs.3.rs-7819613/v1","is_oa":true,"landing_page_url":"https://doi.org/10.21203/rs.3.rs-7819613/v1","pdf_url":"https://www.researchsquare.com/article/rs-7819613/latest.pdf","source":{"id":"https://openalex.org/S4306525896","display_name":"Research Square","issn_l":null,"issn":null,"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","license_id":"https://openalex.org/licenses/cc-by","version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"Research Square","raw_type":"posted-content"},"sustainable_development_goals":[],"study_designs":[],"awards":[],"funders":[],"has_content":{"grobid_xml":true,"pdf":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4415495458.pdf","grobid_xml":"https://content.openalex.org/works/W4415495458.grobid-xml"},"referenced_works_count":0,"referenced_works":[],"related_works":["https://openalex.org/W1988528758","https://openalex.org/W1607440177","https://openalex.org/W2791997759","https://openalex.org/W2342462526","https://openalex.org/W2949292620","https://openalex.org/W2941833243","https://openalex.org/W3196134858","https://openalex.org/W2523847180","https://openalex.org/W3166137549","https://openalex.org/W2045832011"],"abstract_inverted_index":{"Abstract":[0],"The":[1,29,139,187,216],"amide":[2,87,142],"bond":[3,125],"represents":[4],"the":[5,37,46,50,57,71,75,123,131,151,193,201,211,222],"most":[6,38,51],"fundamental":[7],"functional":[8,97,178],"group":[9,179],"in":[10,45,107,240],"chemistry":[11],"and":[12,25,62,114,176,184,229],"biology.":[13],"Amides":[14],"are":[15],"key":[16,76],"building":[17,238],"blocks":[18,239],"of":[19,31,59,74,94,196,203,213,224,234],"peptides,":[20],"pharmaceuticals,":[21],"polymers,":[22],"advanced":[23],"materials":[24],"biologically":[26],"active":[27],"compounds.":[28],"synthesis":[30,88,143,162,202,212,223],"amides":[32,225,235],"has":[33,66],"been":[34,67],"ranked":[35],"as":[36,236],"common":[39,52],"reaction":[40,152],"performed":[41],"by":[42,54,70,117,127,147,163,170,226],"synthetic":[43],"chemists":[44],"last":[47,132],"century.":[48],"While":[49],"approach":[53,65,85,167],"far":[55],"involves":[56],"condensation":[58],"carboxylic":[60,77,95],"acids":[61,105],"amines,":[63],"this":[64,197,206],"historically":[68],"limited":[69],"positional":[72],"connectivity":[73],"acid":[78,96],"group.":[79,98],"Herein,":[80],"we":[81],"report":[82],"a":[83,111,159,171],"new":[84,198,219],"to":[86,110,158,210],"that":[89,102],"relies":[90],"on":[91],"molecular":[92],"shuffling":[93],"It":[99],"is":[100,144,168,189,208],"found":[101],"amino":[103],"benzoic":[104],"engage":[106],"oxidative":[108],"addition":[109],"Pd(0)":[112],"complex,":[113],"CO":[115],"generated":[116],"decarbonylation":[118],"undergoes":[119],"transfer":[120],"insertion":[121,129],"into":[122],"C\u2013Pd":[124],"formed":[126],"alkene":[128],"before":[130],"reductive":[133],"elimination,":[134],"achieving":[135],"carbonyl":[136,140,227],"shuttle":[137,141],"amidation.":[138],"precisely":[145],"controlled":[146],"ligand":[148],"selection,":[149],"where":[150],"pathway":[153],"can":[154],"be":[155],"fully":[156],"switched":[157],"divergent":[160],"amine":[161],"decarbonylative":[164],"amination.":[165],"This":[166],"characterized":[169],"particularly":[172],"wide":[173],"substrate":[174],"scope":[175],"excellent":[177],"tolerance,":[180],"including":[181],"bioactive":[182],"molecules":[183],"late-stage":[185],"functionalization.":[186],"method":[188,199],"scalable,":[190],"which":[191],"highlights":[192],"practical":[194],"utility":[195],"for":[200,221],"amides.":[204,215],"Moreover,":[205],"strategy":[207],"applicable":[209],"linear":[214],"study":[217],"opens":[218],"avenues":[220],"reshuffling":[228],"advances":[230],"an":[231],"accelerated":[232],"utilization":[233],"critical":[237],"chemical":[241],"science.":[242]},"counts_by_year":[],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2025-10-24T00:00:00"}
