{"id":"https://openalex.org/W4311290179","doi":"https://doi.org/10.1039/d2ra07003k","title":"The design of experiments (DoE) in optimization of an aerobic flow Pd-catalyzed oxidation of alcohol towards an important aldehyde precursor in the synthesis of phosphatidylinositide 3-kinase inhibitor (CPL302415)","display_name":"The design of experiments (DoE) in optimization of an aerobic flow Pd-catalyzed oxidation of alcohol towards an important aldehyde precursor in the synthesis of phosphatidylinositide 3-kinase inhibitor (CPL302415)","publication_year":2022,"publication_date":"2022-01-01","ids":{"openalex":"https://openalex.org/W4311290179","doi":"https://doi.org/10.1039/d2ra07003k","pmid":"https://pubmed.ncbi.nlm.nih.gov/36505705","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/9682622"},"language":"en","primary_location":{"id":"doi:10.1039/d2ra07003k","doi":"https://doi.org/10.1039/d2ra07003k","is_oa":true,"landing_page_url":"https://doi.org/10.1039/d2ra07003k","pdf_url":"https://pubs.rsc.org/en/content/articlepdf/2022/ra/d2ra07003k","source":{"id":"https://openalex.org/S2481244646","display_name":"RSC Advances","issn_l":"2046-2069","issn":["2046-2069"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["cwts-core","doaj","dongbi-c","jufo-1","ki-jl-1","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"RSC Advances","raw_type":"journal-article"},"volume":null,"type":"article","is_traditional":true,"indexed_in":["crossref","doaj","pubmed"],"open_access":{"is_oa":true,"oa_status":"gold","oa_url":"https://pubs.rsc.org/en/content/articlepdf/2022/ra/d2ra07003k","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5018645224","display_name":"Stanis\u0142aw Micha\u0142ek","orcid":"https://orcid.org/0000-0002-6648-0604","observed_orcids":["https://orcid.org/0000-0002-6648-0604"]},"institutions":[{"id":"https://openalex.org/I108403487","display_name":"Warsaw University of Technology","ror":"https://ror.org/00y0xnp53","country_code":"PL","type":"education","lineage":["https://openalex.org/I108403487"]},{"id":"https://openalex.org/I4210096162","display_name":"Celon Pharma (Poland)","ror":"https://ror.org/00y35qw13","country_code":"PL","type":"company","lineage":["https://openalex.org/I4210096162"]}],"countries":["PL"],"is_corresponding":false,"raw_author_name":"Stanis\u0142aw Micha\u0142ek","raw_affiliation_strings":["Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","Faculty of Chemistry, Warsaw University of Technology, Ul. Noakowskiego 3, 00-664 Warsaw, Poland"],"raw_orcid":"https://orcid.org/0000-0002-6648-0604","affiliations":[{"raw_affiliation_string":"Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","institution_ids":["https://openalex.org/I4210096162"]},{"raw_affiliation_string":"Faculty of Chemistry, Warsaw University of Technology, Ul. Noakowskiego 3, 00-664 Warsaw, Poland","institution_ids":["https://openalex.org/I108403487"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5047764683","display_name":"Lidia Gurba-Bry\u015bkiewicz","orcid":"https://orcid.org/0000-0002-7807-6641","observed_orcids":["https://orcid.org/0000-0002-7807-6641"]},"institutions":[{"id":"https://openalex.org/I4210096162","display_name":"Celon Pharma (Poland)","ror":"https://ror.org/00y35qw13","country_code":"PL","type":"company","lineage":["https://openalex.org/I4210096162"]}],"countries":["PL"],"is_corresponding":false,"raw_author_name":"Lidia Gurba-Bry\u015bkiewicz","raw_affiliation_strings":["Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland"],"raw_orcid":"https://orcid.org/0000-0002-7807-6641","affiliations":[{"raw_affiliation_string":"Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","institution_ids":["https://openalex.org/I4210096162"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5022253744","display_name":"Wioleta Maruszak","orcid":"https://orcid.org/0000-0002-4922-4465","observed_orcids":["https://orcid.org/0000-0002-4922-4465"]},"institutions":[{"id":"https://openalex.org/I4210096162","display_name":"Celon Pharma (Poland)","ror":"https://ror.org/00y35qw13","country_code":"PL","type":"company","lineage":["https://openalex.org/I4210096162"]}],"countries":["PL"],"is_corresponding":false,"raw_author_name":"Wioleta Maruszak","raw_affiliation_strings":["Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland"],"raw_orcid":"https://orcid.org/0000-0002-4922-4465","affiliations":[{"raw_affiliation_string":"Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","institution_ids":["https://openalex.org/I4210096162"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5007817584","display_name":"Marcin Zagozda","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210096162","display_name":"Celon Pharma (Poland)","ror":"https://ror.org/00y35qw13","country_code":"PL","type":"company","lineage":["https://openalex.org/I4210096162"]}],"countries":["PL"],"is_corresponding":false,"raw_author_name":"Marcin Zagozda","raw_affiliation_strings":["Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","institution_ids":["https://openalex.org/I4210096162"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5101561812","display_name":"Anna M. Maj","orcid":"https://orcid.org/0000-0002-7875-6751","observed_orcids":["https://orcid.org/0000-0002-7875-6751"]},"institutions":[{"id":"https://openalex.org/I4210096162","display_name":"Celon Pharma (Poland)","ror":"https://ror.org/00y35qw13","country_code":"PL","type":"company","lineage":["https://openalex.org/I4210096162"]}],"countries":["PL"],"is_corresponding":true,"raw_author_name":"Anna M. Maj","raw_affiliation_strings":["Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland"],"raw_orcid":"https://orcid.org/0000-0002-7875-6751","affiliations":[{"raw_affiliation_string":"Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","institution_ids":["https://openalex.org/I4210096162"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5028999728","display_name":"Zbigniew Ochal","orcid":"https://orcid.org/0000-0002-2723-3782","observed_orcids":["https://orcid.org/0000-0002-2723-3782"]},"institutions":[{"id":"https://openalex.org/I108403487","display_name":"Warsaw University of Technology","ror":"https://ror.org/00y0xnp53","country_code":"PL","type":"education","lineage":["https://openalex.org/I108403487"]}],"countries":["PL"],"is_corresponding":false,"raw_author_name":"Zbigniew Ochal","raw_affiliation_strings":["Faculty of Chemistry, Warsaw University of Technology, Ul. Noakowskiego 3, 00-664 Warsaw, Poland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Faculty of Chemistry, Warsaw University of Technology, Ul. Noakowskiego 3, 00-664 Warsaw, Poland","institution_ids":["https://openalex.org/I108403487"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5113859891","display_name":"KRZYSZTOF K. DUBIEL","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210096162","display_name":"Celon Pharma (Poland)","ror":"https://ror.org/00y35qw13","country_code":"PL","type":"company","lineage":["https://openalex.org/I4210096162"]}],"countries":["PL"],"is_corresponding":false,"raw_author_name":"Krzysztof Dubiel","raw_affiliation_strings":["Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","institution_ids":["https://openalex.org/I4210096162"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5074594600","display_name":"Maciej Wieczorek","orcid":null,"observed_orcids":[]},"institutions":[{"id":"https://openalex.org/I4210096162","display_name":"Celon Pharma (Poland)","ror":"https://ror.org/00y35qw13","country_code":"PL","type":"company","lineage":["https://openalex.org/I4210096162"]}],"countries":["PL"],"is_corresponding":false,"raw_author_name":"Maciej Wieczorek","raw_affiliation_strings":["Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Celon Pharma S.A., Ul. Marymoncka 15, 05-152 Kazu\u0144 Nowy, Poland","institution_ids":["https://openalex.org/I4210096162"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5101561812"],"corresponding_institution_ids":["https://openalex.org/I4210096162"],"apc_list":{"value":850,"currency":"GBP","value_usd":1042},"apc_paid":{"value":850,"currency":"GBP","value_usd":1042},"fwci":0.8316,"has_fulltext":true,"cited_by_count":9,"citation_normalized_percentile":{"value":0.6210273,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":89,"max":98},"biblio":{"volume":"12","issue":"52","first_page":"33605","last_page":"33611"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11989","display_name":"Oxidative Organic Chemistry Reactions","score":0.9340999722480774,"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/T11989","display_name":"Oxidative Organic Chemistry Reactions","score":0.9340999722480774,"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/T10404","display_name":"Enzyme Catalysis and Immobilization","score":0.025100000202655792,"subfield":{"id":"https://openalex.org/subfields/1312","display_name":"Molecular Biology"},"field":{"id":"https://openalex.org/fields/13","display_name":"Biochemistry, Genetics and Molecular Biology"},"domain":{"id":"https://openalex.org/domains/1","display_name":"Life Sciences"}},{"id":"https://openalex.org/T11831","display_name":"Chemical Synthesis and Reactions","score":0.008899999782443047,"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/palladium-catalysis","display_name":"palladium catalysis","score":0.8690000176429749},{"id":"https://openalex.org/keywords/aerobic-oxidation","display_name":"aerobic oxidation","score":0.8529999852180481},{"id":"https://openalex.org/keywords/alcohol-oxidation","display_name":"alcohol oxidation","score":0.9279999732971191},{"id":"https://openalex.org/keywords/aldehyde-synthesis","display_name":"aldehyde synthesis","score":0.828000009059906},{"id":"https://openalex.org/keywords/pi3k-inhibitors","display_name":"PI3K inhibitors","score":0.9440000057220459},{"id":"https://openalex.org/keywords/green-chemistry","display_name":"green chemistry","score":0.6660000085830688},{"id":"https://openalex.org/keywords/e-factor","display_name":"E-factor","score":0.6899999976158142},{"id":"https://openalex.org/keywords/waste-reduction","display_name":"waste reduction","score":0.675000011920929},{"id":"https://openalex.org/keywords/catalytic-oxidation","display_name":"catalytic oxidation","score":0.6269999742507935}],"concepts":[{"id":"https://openalex.org/C2779825165","wikidata":"https://www.wikidata.org/wiki/Q101497","display_name":"Aldehyde","level":3,"score":0.8516188859939575},{"id":"https://openalex.org/C2781066024","wikidata":"https://www.wikidata.org/wiki/Q156","display_name":"Alcohol","level":2,"score":0.6574295163154602},{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.6235513091087341},{"id":"https://openalex.org/C114157696","wikidata":"https://www.wikidata.org/wiki/Q3082836","display_name":"Alcohol oxidation","level":3,"score":0.5533890724182129},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.5278011560440063},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.4306046664714813},{"id":"https://openalex.org/C184235292","wikidata":"https://www.wikidata.org/wiki/Q421851","display_name":"Kinase","level":2,"score":0.41377368569374084},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.33798646926879883},{"id":"https://openalex.org/C55493867","wikidata":"https://www.wikidata.org/wiki/Q7094","display_name":"Biochemistry","level":1,"score":0.3034684658050537}],"mesh":[],"locations_count":3,"locations":[{"id":"doi:10.1039/d2ra07003k","doi":"https://doi.org/10.1039/d2ra07003k","is_oa":true,"landing_page_url":"https://doi.org/10.1039/d2ra07003k","pdf_url":"https://pubs.rsc.org/en/content/articlepdf/2022/ra/d2ra07003k","source":{"id":"https://openalex.org/S2481244646","display_name":"RSC Advances","issn_l":"2046-2069","issn":["2046-2069"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["cwts-core","doaj","dongbi-c","jufo-1","ki-jl-1","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"RSC Advances","raw_type":"journal-article"},{"id":"pmid:36505705","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/36505705","pdf_url":null,"source":{"id":"https://openalex.org/S4306525036","display_name":"PubMed","issn_l":null,"issn":null,"is_oa":false,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"RSC advances","raw_type":"Journal Article"},{"id":"pmh:oai:pubmedcentral.nih.gov:9682622","doi":null,"is_oa":true,"landing_page_url":"https://pmc.ncbi.nlm.nih.gov/articles/PMC9682622/","pdf_url":null,"source":{"id":"https://openalex.org/S2764455111","display_name":"PubMed Central","issn_l":null,"issn":null,"is_oa":true,"is_in_doaj":false,"is_core":false,"listed_in":[],"host_organization":"https://openalex.org/I1299303238","host_organization_name":"National Institutes of Health","host_organization_lineage":["https://openalex.org/I1299303238"],"host_organization_lineage_names":[],"type":"repository"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"RSC Adv","raw_type":"Text"}],"best_oa_location":{"id":"doi:10.1039/d2ra07003k","doi":"https://doi.org/10.1039/d2ra07003k","is_oa":true,"landing_page_url":"https://doi.org/10.1039/d2ra07003k","pdf_url":"https://pubs.rsc.org/en/content/articlepdf/2022/ra/d2ra07003k","source":{"id":"https://openalex.org/S2481244646","display_name":"RSC Advances","issn_l":"2046-2069","issn":["2046-2069"],"is_oa":true,"is_in_doaj":true,"is_core":true,"listed_in":["cwts-core","doaj","dongbi-c","jufo-1","ki-jl-1","norway-1","poland-100","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320556","host_organization_name":"Royal Society of Chemistry","host_organization_lineage":["https://openalex.org/P4310320556"],"host_organization_lineage_names":["Royal Society of Chemistry"],"type":"journal"},"license":"cc-by-nc","license_id":"https://openalex.org/licenses/cc-by-nc","version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"RSC Advances","raw_type":"journal-article"},"sustainable_development_goals":[{"id":"https://metadata.un.org/sdg/12","display_name":"Responsible consumption and production","score":0.807699978351593}],"study_designs":[],"awards":[{"id":"https://openalex.org/G7887796180","display_name":null,"funder_award_id":"POIR.01.02.00-00-0085/18-00","funder_id":"https://openalex.org/F4320335039","funder_display_name":"Narodowe Centrum Bada\u0144 i Rozwoju"}],"funders":[{"id":"https://openalex.org/F4320335039","display_name":"Narodowe Centrum Bada\u0144 i Rozwoju","ror":"https://ror.org/05pwfyy15"}],"has_content":{"pdf":true,"grobid_xml":true},"content_urls":{"pdf":"https://content.openalex.org/works/W4311290179.pdf","grobid_xml":"https://content.openalex.org/works/W4311290179.grobid-xml"},"referenced_works_count":39,"referenced_works":["https://openalex.org/W1006037363","https://openalex.org/W1541612385","https://openalex.org/W1550373552","https://openalex.org/W1793575896","https://openalex.org/W1965139687","https://openalex.org/W1971719269","https://openalex.org/W1972565334","https://openalex.org/W1977414920","https://openalex.org/W1979248371","https://openalex.org/W1987751510","https://openalex.org/W2009886463","https://openalex.org/W2018540863","https://openalex.org/W2033020343","https://openalex.org/W2045293316","https://openalex.org/W2071979927","https://openalex.org/W2087066381","https://openalex.org/W2087284555","https://openalex.org/W2097047205","https://openalex.org/W2119146414","https://openalex.org/W2121087867","https://openalex.org/W2124667501","https://openalex.org/W2150286077","https://openalex.org/W2160785918","https://openalex.org/W2168444131","https://openalex.org/W2169624687","https://openalex.org/W2312367709","https://openalex.org/W2332352869","https://openalex.org/W2345099053","https://openalex.org/W2522478136","https://openalex.org/W2767720991","https://openalex.org/W2951109569","https://openalex.org/W2952854780","https://openalex.org/W3012484016","https://openalex.org/W3018941105","https://openalex.org/W3118640016","https://openalex.org/W3127568877","https://openalex.org/W3132439288","https://openalex.org/W3199306128","https://openalex.org/W4288448370"],"related_works":["https://openalex.org/W2952371852","https://openalex.org/W4232918433","https://openalex.org/W4255313531","https://openalex.org/W137103633","https://openalex.org/W2952501965","https://openalex.org/W2949761099","https://openalex.org/W3212906936","https://openalex.org/W1965139687","https://openalex.org/W3093065054","https://openalex.org/W2144738542"],"abstract_inverted_index":{"inhibitor.":[0],"Applying":[1],"this":[2],"environmental-friendly,":[3],"sustainable":[4],"catalytic":[5],"oxidation":[6],"we":[7,21],"significantly":[8],"increased":[9],"product":[10],"yield":[11],"(up":[12,29],"to":[13,30],"84%)":[14],"and":[15,26],"by":[16,42],"eliminating":[17],"of":[18],"workup":[19],"step,":[20],"improved":[22],"the":[23,35,44],"waste":[24],"index":[25],"E":[27],"factor":[28],"0.13)":[31],"in":[32],"comparison":[33],"with":[34],"stoichiometric":[36],"synthesis.":[37],"The":[38],"process":[39],"was":[40],"optimized":[41],"using":[43],"DoE":[45],"approach.":[46]},"counts_by_year":[{"year":2025,"cited_by_count":1},{"year":2024,"cited_by_count":6},{"year":2023,"cited_by_count":2}],"updated_date":"2026-11-10T11:39:43.021295","created_date":"2022-12-25T00:00:00"}
