{"id":"https://openalex.org/W2515013258","doi":"https://doi.org/10.1021/acs.orglett.6b02088","title":"Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino, and Carboxyl Groups via the Nicholas Reaction","display_name":"Alkyne Ligation Handles: Propargylation of Hydroxyl, Sulfhydryl, Amino, and Carboxyl Groups via the Nicholas Reaction","publication_year":2016,"publication_date":"2016-08-29","ids":{"openalex":"https://openalex.org/W2515013258","doi":"https://doi.org/10.1021/acs.orglett.6b02088","mag":"2515013258","pmid":"https://pubmed.ncbi.nlm.nih.gov/27570975","pmcid":"https://www.ncbi.nlm.nih.gov/pmc/articles/5234733"},"language":"en","primary_location":{"id":"doi:10.1021/acs.orglett.6b02088","doi":"https://doi.org/10.1021/acs.orglett.6b02088","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.6b02088","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},"volume":null,"type":"article","indexed_in":["crossref","pubmed"],"open_access":{"is_oa":true,"oa_status":"green","oa_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/5234733","any_repository_has_fulltext":true},"authorships":[{"author_position":"first","author":{"id":"https://openalex.org/A5023587227","display_name":"Sarah Wells","orcid":"https://orcid.org/0000-0002-7580-3655","observed_orcids":["https://orcid.org/0000-0002-7580-3655"]},"institutions":[{"id":"https://openalex.org/I170201317","display_name":"University of Pittsburgh","ror":"https://ror.org/01an3r305","country_code":"US","type":"education","lineage":["https://openalex.org/I170201317"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"Sarah M. Wells","raw_affiliation_strings":["Department\rof Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15206, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department\rof Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15206, United States","institution_ids":["https://openalex.org/I170201317"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5016244640","display_name":"John C. Widen","orcid":"https://orcid.org/0000-0002-8973-1509","observed_orcids":["https://orcid.org/0000-0002-8973-1509"]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]}],"countries":["US"],"is_corresponding":false,"raw_author_name":"John C. Widen","raw_affiliation_strings":["Department\rof Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department\rof Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States","institution_ids":["https://openalex.org/I130238516"]}]},{"author_position":"middle","author":{"id":"https://openalex.org/A5009655060","display_name":"Daniel A. Harki","orcid":"https://orcid.org/0000-0001-5950-931X","observed_orcids":["https://orcid.org/0000-0001-5950-931X"]},"institutions":[{"id":"https://openalex.org/I130238516","display_name":"University of Minnesota","ror":"https://ror.org/017zqws13","country_code":"US","type":"education","lineage":["https://openalex.org/I130238516"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Daniel A. Harki","raw_affiliation_strings":["Department\rof Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department\rof Medicinal Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, United States","institution_ids":["https://openalex.org/I130238516"]}]},{"author_position":"last","author":{"id":"https://openalex.org/A5070043526","display_name":"Kay M. Brummond","orcid":"https://orcid.org/0000-0003-3595-6806","observed_orcids":["https://orcid.org/0000-0003-3595-6806"]},"institutions":[{"id":"https://openalex.org/I170201317","display_name":"University of Pittsburgh","ror":"https://ror.org/01an3r305","country_code":"US","type":"education","lineage":["https://openalex.org/I170201317"]}],"countries":["US"],"is_corresponding":true,"raw_author_name":"Kay M. Brummond","raw_affiliation_strings":["Department\rof Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15206, United States"],"raw_orcid":null,"affiliations":[{"raw_affiliation_string":"Department\rof Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15206, United States","institution_ids":["https://openalex.org/I170201317"]}]}],"institutions":[],"countries_distinct_count":1,"institutions_distinct_count":2,"corresponding_author_ids":["https://openalex.org/A5009655060","https://openalex.org/A5070043526"],"corresponding_institution_ids":["https://openalex.org/I130238516","https://openalex.org/I170201317"],"apc_list":{"value":4500,"currency":"USD","value_usd":4500},"apc_paid":null,"fwci":1.0695,"has_fulltext":false,"cited_by_count":14,"citation_normalized_percentile":{"value":0.73917497,"is_in_top_1_percent":false,"is_in_top_10_percent":false},"cited_by_percentile_year":{"min":88,"max":96},"biblio":{"volume":"18","issue":"18","first_page":"4566","last_page":"4569"},"is_retracted":false,"is_paratext":false,"is_xpac":false,"primary_topic":{"id":"https://openalex.org/T11440","display_name":"Click Chemistry and Applications","score":0.986299991607666,"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/T11440","display_name":"Click Chemistry and Applications","score":0.986299991607666,"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/T10871","display_name":"Catalytic Alkyne Reactions","score":0.004999999888241291,"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":0.0017999999690800905,"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/nicholas-reaction","display_name":"Nicholas reaction","score":0.8939999938011169},{"id":"https://openalex.org/keywords/propargylation","display_name":"propargylation","score":0.8519999980926514},{"id":"https://openalex.org/keywords/propargyl-group","display_name":"propargyl group","score":0.7680000066757202},{"id":"https://openalex.org/keywords/bioorthogonal-chemistry","display_name":"bioorthogonal chemistry","score":0.6940000057220459},{"id":"https://openalex.org/keywords/dicobalt-hexacarbonyl","display_name":"dicobalt hexacarbonyl","score":0.9259999990463257},{"id":"https://openalex.org/keywords/hydroxyl-groups","display_name":"hydroxyl groups","score":0.8040000200271606},{"id":"https://openalex.org/keywords/sulfhydryl-groups","display_name":"sulfhydryl groups","score":0.8799999952316284},{"id":"https://openalex.org/keywords/amino-groups","display_name":"amino groups","score":0.9909999966621399},{"id":"https://openalex.org/keywords/carboxyl-groups","display_name":"carboxyl groups","score":0.949999988079071}],"concepts":[{"id":"https://openalex.org/C185592680","wikidata":"https://www.wikidata.org/wiki/Q2329","display_name":"Chemistry","level":0,"score":0.9150816202163696},{"id":"https://openalex.org/C2779012754","wikidata":"https://www.wikidata.org/wiki/Q159226","display_name":"Alkyne","level":3,"score":0.9119826555252075},{"id":"https://openalex.org/C2780437523","wikidata":"https://www.wikidata.org/wiki/Q422660","display_name":"Propargyl","level":3,"score":0.8598151206970215},{"id":"https://openalex.org/C40875361","wikidata":"https://www.wikidata.org/wiki/Q2356542","display_name":"Reagent","level":2,"score":0.6607136726379395},{"id":"https://openalex.org/C21951064","wikidata":"https://www.wikidata.org/wiki/Q899212","display_name":"Combinatorial chemistry","level":1,"score":0.6181201934814453},{"id":"https://openalex.org/C32909587","wikidata":"https://www.wikidata.org/wiki/Q11369","display_name":"Molecule","level":2,"score":0.6111449003219604},{"id":"https://openalex.org/C188198153","wikidata":"https://www.wikidata.org/wiki/Q1613840","display_name":"Limiting","level":2,"score":0.5012092590332031},{"id":"https://openalex.org/C42058472","wikidata":"https://www.wikidata.org/wiki/Q810214","display_name":"Base (topology)","level":2,"score":0.4538416564464569},{"id":"https://openalex.org/C2777332933","wikidata":"https://www.wikidata.org/wiki/Q170409","display_name":"Functional group","level":3,"score":0.4178870618343353},{"id":"https://openalex.org/C179437574","wikidata":"https://www.wikidata.org/wiki/Q15089798","display_name":"Ligation","level":2,"score":0.4103570282459259},{"id":"https://openalex.org/C178790620","wikidata":"https://www.wikidata.org/wiki/Q11351","display_name":"Organic chemistry","level":1,"score":0.3096645176410675},{"id":"https://openalex.org/C161790260","wikidata":"https://www.wikidata.org/wiki/Q82264","display_name":"Catalysis","level":2,"score":0.1093558669090271},{"id":"https://openalex.org/C33923547","wikidata":"https://www.wikidata.org/wiki/Q395","display_name":"Mathematics","level":0,"score":0.0},{"id":"https://openalex.org/C153911025","wikidata":"https://www.wikidata.org/wiki/Q7202","display_name":"Molecular biology","level":1,"score":0.0},{"id":"https://openalex.org/C78519656","wikidata":"https://www.wikidata.org/wiki/Q101333","display_name":"Mechanical engineering","level":1,"score":0.0},{"id":"https://openalex.org/C86803240","wikidata":"https://www.wikidata.org/wiki/Q420","display_name":"Biology","level":0,"score":0.0},{"id":"https://openalex.org/C521977710","wikidata":"https://www.wikidata.org/wiki/Q81163","display_name":"Polymer","level":2,"score":0.0},{"id":"https://openalex.org/C134306372","wikidata":"https://www.wikidata.org/wiki/Q7754","display_name":"Mathematical analysis","level":1,"score":0.0},{"id":"https://openalex.org/C127413603","wikidata":"https://www.wikidata.org/wiki/Q11023","display_name":"Engineering","level":0,"score":0.0}],"mesh":[{"descriptor_ui":"D000480","descriptor_name":"Alkynes","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D002248","descriptor_name":"Carbon Monoxide","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D003035","descriptor_name":"Cobalt","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D010293","descriptor_name":"Pargyline","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":false},{"descriptor_ui":"D010293","descriptor_name":"Pargyline","qualifier_ui":"Q000138","qualifier_name":"chemical synthesis","is_major_topic":true},{"descriptor_ui":"D010293","descriptor_name":"Pargyline","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":false},{"descriptor_ui":"D011392","descriptor_name":"Proline","qualifier_ui":"Q000031","qualifier_name":"analogs & derivatives","is_major_topic":false},{"descriptor_ui":"D011392","descriptor_name":"Proline","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D013438","descriptor_name":"Sulfhydryl Compounds","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true},{"descriptor_ui":"D015394","descriptor_name":"Molecular Structure","qualifier_ui":null,"qualifier_name":null,"is_major_topic":false},{"descriptor_ui":"D017665","descriptor_name":"Hydroxyl Radical","qualifier_ui":"Q000737","qualifier_name":"chemistry","is_major_topic":true}],"locations_count":3,"locations":[{"id":"doi:10.1021/acs.orglett.6b02088","doi":"https://doi.org/10.1021/acs.orglett.6b02088","is_oa":false,"landing_page_url":"https://doi.org/10.1021/acs.orglett.6b02088","pdf_url":null,"source":{"id":"https://openalex.org/S201989124","display_name":"Organic Letters","issn_l":"1523-7052","issn":["1523-7052","1523-7060"],"is_oa":false,"is_in_doaj":false,"is_core":true,"listed_in":["cwts-core","dongbi-a","jufo-2","ki-jl-2","medline","norway-2","poland-140","russia-white-list-1","vabb-shw"],"host_organization":"https://openalex.org/P4310320006","host_organization_name":"American Chemical Society","host_organization_lineage":["https://openalex.org/P4310320006"],"host_organization_lineage_names":["American Chemical Society"],"type":"journal"},"license":null,"license_id":null,"version":"publishedVersion","is_accepted":true,"is_published":true,"raw_source_name":"Organic Letters","raw_type":"journal-article"},{"id":"pmid:27570975","doi":null,"is_oa":false,"landing_page_url":"https://pubmed.ncbi.nlm.nih.gov/27570975","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":"Organic letters","raw_type":"Journal Article"},{"id":"pmh:oai:pubmedcentral.nih.gov:5234733","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/5234733","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":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"Org Lett","raw_type":"Text"}],"best_oa_location":{"id":"pmh:oai:pubmedcentral.nih.gov:5234733","doi":null,"is_oa":true,"landing_page_url":"https://www.ncbi.nlm.nih.gov/pmc/articles/5234733","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":null,"license_id":null,"version":"acceptedVersion","is_accepted":true,"is_published":false,"raw_source_name":"Org Lett","raw_type":"Text"},"sustainable_development_goals":[],"study_designs":[],"awards":[{"id":"https://openalex.org/G352283167","display_name":"Allenic [2 + 2 + 1] Reactions Enabling Syntheses of Natural Products with 7-Membe","funder_award_id":"R01GM054161","funder_id":"https://openalex.org/F4320337354","funder_display_name":"National Institute of General Medical Sciences"},{"id":"https://openalex.org/G5302978274","display_name":"CHEMOPROTEOMICS PROFILING OF PARTHENOLIDE IN HUMAN GLIOBLASTOMA","funder_award_id":"R21CA194661","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"},{"id":"https://openalex.org/G7214754510","display_name":null,"funder_award_id":"PC141033","funder_id":"https://openalex.org/F4320306078","funder_display_name":"U.S. Department of Defense"},{"id":"https://openalex.org/G9000895342","display_name":"Cancer Center Support Grant","funder_award_id":"P30CA077598","funder_id":"https://openalex.org/F4320337351","funder_display_name":"National Cancer Institute"}],"funders":[{"id":"https://openalex.org/F4320306078","display_name":"U.S. Department of Defense","ror":"https://ror.org/0447fe631"},{"id":"https://openalex.org/F4320337351","display_name":"National Cancer Institute","ror":"https://ror.org/040gcmg81"},{"id":"https://openalex.org/F4320337354","display_name":"National Institute of General Medical Sciences","ror":"https://ror.org/04q48ey07"}],"has_content":{"pdf":false,"grobid_xml":false},"content_urls":null,"referenced_works_count":45,"referenced_works":["https://openalex.org/W1724225678","https://openalex.org/W1967176639","https://openalex.org/W1982225489","https://openalex.org/W1982245794","https://openalex.org/W1986239448","https://openalex.org/W1986474924","https://openalex.org/W1987626919","https://openalex.org/W1987850726","https://openalex.org/W1990715466","https://openalex.org/W2006055454","https://openalex.org/W2007516858","https://openalex.org/W2019380309","https://openalex.org/W2019410402","https://openalex.org/W2023557482","https://openalex.org/W2036674484","https://openalex.org/W2040343490","https://openalex.org/W2040473505","https://openalex.org/W2042191236","https://openalex.org/W2042199136","https://openalex.org/W2053558674","https://openalex.org/W2055474081","https://openalex.org/W2055603497","https://openalex.org/W2062604710","https://openalex.org/W2067570105","https://openalex.org/W2070582970","https://openalex.org/W2076739074","https://openalex.org/W2092560787","https://openalex.org/W2093552525","https://openalex.org/W2096385751","https://openalex.org/W2097816664","https://openalex.org/W2107627113","https://openalex.org/W2124565687","https://openalex.org/W2141247194","https://openalex.org/W2145662716","https://openalex.org/W2149554987","https://openalex.org/W2149609961","https://openalex.org/W2151709132","https://openalex.org/W2171053944","https://openalex.org/W2245195838","https://openalex.org/W2326496230","https://openalex.org/W2329896225","https://openalex.org/W2951029211","https://openalex.org/W2951106423","https://openalex.org/W2953123588","https://openalex.org/W3151754444"],"related_works":["https://openalex.org/W4320481669","https://openalex.org/W2951346322","https://openalex.org/W4234409399","https://openalex.org/W4220674029","https://openalex.org/W2743627426","https://openalex.org/W2342506021","https://openalex.org/W2953160837","https://openalex.org/W2030643594","https://openalex.org/W1852641833","https://openalex.org/W3156587651"],"abstract_inverted_index":{"The":[0],"Nicholas":[1],"reaction":[2],"has":[3],"been":[4],"applied":[5],"to":[6],"the":[7,43,48,60],"installation":[8],"of":[9,15,35,45,50],"alkyne":[10],"ligation":[11],"handles.":[12],"Acid-promoted":[13],"propargylation":[14],"hydroxyl,":[16],"sulfhydryl,":[17],"amino,":[18],"and":[19,63],"carboxyl":[20],"groups":[21,37],"using":[22],"dicobalt":[23],"hexacarbonyl-stabilized":[24],"propargylium":[25,65],"ions":[26],"is":[27,31],"reported.":[28],"This":[29],"method":[30],"useful":[32],"for":[33,47,52],"introduction":[34],"propargyl":[36],"into":[38],"base-sensitive":[39],"molecules,":[40],"thereby":[41],"expanding":[42],"toolbox":[44],"methods":[46],"incorporation":[49],"alkynes":[51],"bio-orthogonal":[53],"reactions.":[54],"High-value":[55],"molecules":[56],"are":[57,68],"used":[58],"as":[59],"limiting":[61],"reagent,":[62],"various":[64],"ion":[66],"precursors":[67],"compared.":[69]},"counts_by_year":[{"year":2025,"cited_by_count":2},{"year":2023,"cited_by_count":2},{"year":2022,"cited_by_count":1},{"year":2021,"cited_by_count":1},{"year":2020,"cited_by_count":2},{"year":2019,"cited_by_count":1},{"year":2018,"cited_by_count":2},{"year":2017,"cited_by_count":1},{"year":2016,"cited_by_count":2}],"updated_date":"2026-10-31T12:09:11.096373","created_date":"2016-09-16T00:00:00"}