{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,6]],"date-time":"2026-04-06T23:02:07Z","timestamp":1775516527184,"version":"3.50.1"},"reference-count":140,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2018,5,29]],"date-time":"2018-05-29T00:00:00Z","timestamp":1527552000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21332002"],"award-info":[{"award-number":["21332002"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["The Chemical Record"],"published-print":{"date-parts":[[2018,11]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Cu(I)\u2010catalyzed reaction of diazo compounds generates a Cu(I)\u2010carbene intermediate that undergoes diverse transformations. In the past few years, the diazo compounds (or their precursor <jats:italic>N<\/jats:italic>\u2010tosylhydrazones) have been established as cross\u2010coupling partners under transition\u2010metal catalysis, affording various organic compounds. Particularly the breakthrough has been made in allene synthesis by Cu(I)\u2010catalyzed carbene coupling with terminal alkynes. Moreover, the Cu(I)\u2010catalyzed coupling reaction of diazo compounds with terminal alkynes generates allene intermediate that undergoes tandem cyclization\/coupling to afford cyclic compounds. This review article summarizes the most recent developments in allene synthesis based on the Cu(I)\u2010carbene coupling reactions and the utilization of allene intermediates in tandem reactions.<\/jats:p>","DOI":"10.1002\/tcr.201800023","type":"journal-article","created":{"date-parts":[[2018,5,29]],"date-time":"2018-05-29T07:11:08Z","timestamp":1527577868000},"page":"1548-1559","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":54,"title":["Cu(I)\u2010Catalyzed Cross\u2010Coupling of Diazo Compounds with Terminal Alkynes: An Efficient Access to Allenes"],"prefix":"10.1002","volume":"18","author":[{"given":"Mohammad Lokman","family":"Hossain","sequence":"first","affiliation":[{"name":"Department of Chemistry Jagannath University  Dhaka Bangladesh"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jianbo","family":"Wang","sequence":"additional","affiliation":[{"name":"Beijing National Laboratory of Molecular Sciences (BNLMS) Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education College of Chemistry Peking University  Beijing 100871 China"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,5,29]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For selected comprehensive reviews see:"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00028a010"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.199417971"},{"key":"e_1_2_7_4_2","volume-title":"Modern Catalytic Methods for Organic Synthesis with Diazo Compounds","author":"Doyle M. P."},{"key":"e_1_2_7_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100224"},{"key":"e_1_2_7_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr940066a"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.04.074"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.5b00121"},{"key":"e_1_2_7_9_1","unstructured":"\u00a0"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0200217"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature06485"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr900239n"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cs00217h"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.12.78"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)00222-1"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr010007e"},{"key":"e_1_2_7_18_1","unstructured":"\u00a0"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1039\/b000708k"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar030045f"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1039\/b604828p"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2009.12.005"},{"key":"e_1_2_7_23_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2016.11.045"},{"key":"e_1_2_7_24_1","unstructured":"For examples see:"},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo050173c"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0605391"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja057739z"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo050109v"},{"key":"e_1_2_7_29_1","unstructured":"For examples see:"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004923"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201406712"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b02037"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201604194"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.7b02634"},{"key":"e_1_2_7_35_1","unstructured":"\u00a0"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma021169v"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma048293u"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma0607822"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603660"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja073897"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201200069"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs500160c"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1039\/C6CS00737F"},{"key":"e_1_2_7_44_1","unstructured":"For reviews see:"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201001588"},{"key":"e_1_2_7_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007961"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15127D"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar300101k"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs4006666"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo401850q"},{"key":"e_1_2_7_51_2","first-page":"4434","volume":"49","author":"Barroso R.","year":"2017","journal-title":"Synthesis"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00382"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc34406h"},{"key":"e_1_2_7_54_1","unstructured":"For reviews see:"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9902796"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20001016)39:20<3590::AID-ANIE3590>3.0.CO;2-L"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1039\/b103904k"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020133k"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar0200394"},{"key":"e_1_2_7_60_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-816005"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr020024j"},{"key":"e_1_2_7_62_2","first-page":"91","volume":"40","author":"Ma S.","year":"2007","journal-title":"Aldrichimica Acta"},{"key":"e_1_2_7_63_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar800011h"},{"key":"e_1_2_7_64_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900153r"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr1004088"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201101460"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60441a"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3cs60382b"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60333D"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60462D"},{"key":"e_1_2_7_71_1","unstructured":"\u00a0"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200300628"},{"key":"e_1_2_7_73_2","first-page":"870","volume":"11","author":"Kim H.","year":"2008","journal-title":"Curr. Opin. Drug Discovery Dev."},{"key":"e_1_2_7_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/9783527619573.ch18"},{"key":"e_1_2_7_75_1","unstructured":"\u00a0"},{"key":"e_1_2_7_76_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2004.09.094"},{"key":"e_1_2_7_77_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2007-965963"},{"key":"e_1_2_7_78_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetasy.2008.11.039"},{"key":"e_1_2_7_79_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CC05640E"},{"key":"e_1_2_7_80_2","first-page":"42","author":"Tejedor D.","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"e_1_2_7_81_2","doi-asserted-by":"publisher","DOI":"10.1021\/cs401007m"},{"key":"e_1_2_7_82_2","doi-asserted-by":"publisher","DOI":"10.1039\/C3CS60429B"},{"key":"e_1_2_7_83_1","unstructured":"For selected examples see:"},{"key":"e_1_2_7_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00178a029"},{"key":"e_1_2_7_85_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja990426h"},{"key":"e_1_2_7_86_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200603739"},{"key":"e_1_2_7_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja800986m"},{"key":"e_1_2_7_88_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja8035527"},{"key":"e_1_2_7_89_2","first-page":"10","author":"Lo V. K. Y.","year":"2008","journal-title":"Org. Lett."},{"key":"e_1_2_7_90_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802445p"},{"key":"e_1_2_7_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol802280c"},{"key":"e_1_2_7_92_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja901528b"},{"key":"e_1_2_7_93_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906189h"},{"key":"e_1_2_7_94_2","first-page":"46","author":"Lo V. K. Y.","year":"2010","journal-title":"Chem. Commun."},{"key":"e_1_2_7_95_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja1020469"},{"key":"e_1_2_7_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300886k"},{"key":"e_1_2_7_97_1","unstructured":"\u00a0"},{"key":"e_1_2_7_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01040a033"},{"key":"e_1_2_7_99_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39770000761"},{"key":"e_1_2_7_100_2","doi-asserted-by":"publisher","DOI":"10.1039\/C39790000859"},{"key":"e_1_2_7_101_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)93581-6"},{"key":"e_1_2_7_102_1","unstructured":"\u00a0"},{"key":"e_1_2_7_103_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2002-33656"},{"key":"e_1_2_7_104_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802391x"},{"key":"e_1_2_7_105_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja910503k"},{"key":"e_1_2_7_106_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201100772"},{"key":"e_1_2_7_107_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300296k"},{"key":"e_1_2_7_108_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2ob26291f"},{"key":"e_1_2_7_109_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201201948"},{"key":"e_1_2_7_110_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1338412"},{"key":"e_1_2_7_111_1","unstructured":"\u00a0"},{"key":"e_1_2_7_112_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0055061"},{"key":"e_1_2_7_113_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0705809104"},{"key":"e_1_2_7_114_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200454070"},{"key":"e_1_2_7_115_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201005741"},{"key":"e_1_2_7_116_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol2006242"},{"key":"e_1_2_7_117_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo3024686"},{"key":"e_1_2_7_118_1","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201300340"},{"key":"e_1_2_7_119_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501538"},{"key":"e_1_2_7_120_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2015.10.043"},{"key":"e_1_2_7_121_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo502316q"},{"key":"e_1_2_7_122_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol102121j"},{"key":"e_1_2_7_123_1","unstructured":"\u00a0"},{"key":"e_1_2_7_124_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo060672t"},{"key":"e_1_2_7_125_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo061525y"},{"key":"e_1_2_7_126_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0035-1561298"},{"key":"e_1_2_7_127_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201501918"},{"key":"e_1_2_7_128_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09674"},{"key":"e_1_2_7_129_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611067"},{"key":"e_1_2_7_130_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol0620850"},{"key":"e_1_2_7_131_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo201942r"},{"key":"e_1_2_7_132_1","unstructured":"\u00a0"},{"key":"e_1_2_7_133_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar020133k"},{"key":"e_1_2_7_134_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr1004088"},{"key":"e_1_2_7_135_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar900153r"},{"key":"e_1_2_7_136_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol103009n"},{"key":"e_1_2_7_137_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol201788v"},{"key":"e_1_2_7_138_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200045"},{"key":"e_1_2_7_139_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo501489c"},{"key":"e_1_2_7_140_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1872-2067(16)62565-2"}],"container-title":["The Chemical Record"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Ftcr.201800023","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tcr.201800023","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/tcr.201800023","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tcr.201800023","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,10]],"date-time":"2023-09-10T20:15:53Z","timestamp":1694376953000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/tcr.201800023"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,5,29]]},"references-count":140,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2018,11]]}},"alternative-id":["10.1002\/tcr.201800023"],"URL":"https:\/\/doi.org\/10.1002\/tcr.201800023","archive":["Portico"],"relation":{},"ISSN":["1527-8999","1528-0691"],"issn-type":[{"value":"1527-8999","type":"print"},{"value":"1528-0691","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,5,29]]},"assertion":[{"value":"2018-03-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-05-09","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-05-29","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}