{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T00:35:33Z","timestamp":1791246933977,"version":"4.1.0"},"reference-count":92,"publisher":"Wiley","issue":"22","license":[{"start":{"date-parts":[[2015,3,20]],"date-time":"2015-03-20T00:00:00Z","timestamp":1426809600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2015,5,26]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A novel approach to agrochemically important difluoromethyl\u2010substituted pyrazoles has been developed based on the elusive reagent CF\n                    <jats:sub>2<\/jats:sub>\n                    HCHN\n                    <jats:sub>2<\/jats:sub>\n                    , which was synthesized (generated in\u2005situ) for the first time and employed in [3+2]\u2005cycloaddition reactions with alkynes. The reaction is extremely practical as it is a one\u2010pot process, does not require a catalyst or the isolation of the potentially toxic and explosive gaseous intermediate, and proceeds in a common solvent, namely chloroform, in air. The reaction is also scalable and allows for the preparation of the target pyrazoles on gram scale.\n                  <\/jats:p>","DOI":"10.1002\/anie.201501529","type":"journal-article","created":{"date-parts":[[2015,3,20]],"date-time":"2015-03-20T21:29:29Z","timestamp":1426886969000},"page":"6558-6561","source":"Crossref","is-referenced-by-count":149,"title":["In\u2005Situ Generation of Difluoromethyl Diazomethane for [3+2]\u2005Cycloadditions with Alkynes"],"prefix":"10.1002","volume":"54","author":[{"given":"Pavel K.","family":"Mykhailiuk","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2015,3,20]]},"reference":[{"key":"e_1_2_2_1_2","unstructured":"\u00a0"},{"key":"e_1_2_2_2_2","volume-title":"Bioorganic and Medicinal Chemistry of Fluorine","year":"2008"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/9781444312096"},{"key":"e_1_2_2_4_2","volume-title":"Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications","year":"2012"},{"key":"e_1_2_2_5_2","unstructured":"\u00a0"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200301023"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2006.01.011"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/op700134j"},{"key":"e_1_2_2_9_2","doi-asserted-by":"publisher","DOI":"10.1039\/B610213C"},{"key":"e_1_2_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm800219f"},{"key":"e_1_2_2_11_2","doi-asserted-by":"publisher","DOI":"10.1093\/nar\/gkm958"},{"key":"e_1_2_2_12_2","unstructured":"\u00a0"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030143e"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101535"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr5002386"},{"key":"e_1_2_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr1004293"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr500223h"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201404005"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2011.01.002"},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100166a"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01248a005"},{"key":"e_1_2_2_22_2","unstructured":"For reports by Carreira and co\u2010workers on the use of CF3CHN2 see:"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905573"},{"key":"e_1_2_2_23_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200905573"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201000787"},{"key":"e_1_2_2_24_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201000787"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004269"},{"key":"e_1_2_2_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201004269"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200983s"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201103526"},{"key":"e_1_2_2_27_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201103526"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202423s"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol300539e"},{"key":"e_1_2_2_30_2","first-page":"1857","author":"Hamilton J. Y.","year":"2013","journal-title":"Synthesis"},{"key":"e_1_2_2_31_2","unstructured":"For contributions from Ma et\u2005al. on the use of CF3CHN2 see:"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202372"},{"key":"e_1_2_2_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201202372"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201301870"},{"key":"e_1_2_2_33_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201301870"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403073"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol501249h"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol500203m"},{"key":"e_1_2_2_37_2","unstructured":"L. Sun J. Nie Y. Zheng J.\u2010A. Ma J. Fluorine Chem.\u00ad2015 DOI:."},{"key":"e_1_2_2_38_2","unstructured":"For contributions of Molander and co\u2010workers on the use of CF3CHN2 see:"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201308036"},{"key":"e_1_2_2_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201308036"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401402d"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201408191"},{"key":"e_1_2_2_41_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201408191"},{"key":"e_1_2_2_42_2","unstructured":"For our contributions on this topic see:"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801022"},{"key":"e_1_2_2_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801022"},{"key":"e_1_2_2_44_2","first-page":"1757","author":"Mykhailiuk P. K.","year":"2008","journal-title":"Synthesis"},{"key":"e_1_2_2_45_2","first-page":"443","author":"Artamonov O. S.","year":"2010","journal-title":"Synthesis"},{"key":"e_1_2_2_46_2","first-page":"225","author":"Artamonov O. S.","year":"2013","journal-title":"Synthesis"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402158"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201301852"},{"key":"e_1_2_2_49_2","unstructured":"For recent contributions of other groups on the use of CF3CHN2 see:"},{"key":"e_1_2_2_50_2","first-page":"1701","author":"Le Maux P.","year":"2006","journal-title":"Synthesis"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2009.12.073"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201000863"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol401636d"},{"key":"e_1_2_2_54_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc35246j"},{"key":"e_1_2_2_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201402597"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo500019a"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1039\/j39710000366"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB02670E"},{"key":"e_1_2_2_59_2","volume-title":"Classics in Total Synthesis III","year":"2011"},{"key":"e_1_2_2_60_2","unstructured":"For some popular difluoromethylation reagents see:"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol202208b"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol503225s"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2004.12.005"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200500101"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-1139(00)82808-0"},{"key":"e_1_2_2_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol070195g"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol900567c"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/ci600423u"},{"key":"e_1_2_2_69_2","unstructured":"Over the past five years difluoromethylated pyrazoles were contained in more than 200 patents of well\u2010known pharmaceutical and agrochemical companies (Reaxys DB)."},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jfluchem.2012.11.008"},{"key":"e_1_2_2_71_2","unstructured":"Recently C2F5CHN2was also generated in aqueous media; see:"},{"key":"e_1_2_2_72_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201304840"},{"key":"e_1_2_2_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/cen-09204-scitech1"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.11.3"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(75)85070-8"},{"key":"e_1_2_2_76_2","doi-asserted-by":"publisher","DOI":"10.1002\/0471221902.ch8"},{"key":"e_1_2_2_77_2","first-page":"57","volume-title":"Prudent Practices for Handling Hazardous Chemicals in Laboratories","year":"1981"},{"key":"e_1_2_2_78_2","unstructured":"CCDC\u20051037925 (3\u2009a) 1037927 (4\u2009a) 1048720 (7\u2009a) 1037926 (12\u2009a) 1048719 (16\u2009a) and 1037928 (17\u2009b) contain the supplementary crystallographic data for this paper. 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