{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T05:14:59Z","timestamp":1790658899296,"version":"4.1.0"},"reference-count":80,"publisher":"Wiley","issue":"15","license":[{"start":{"date-parts":[[2023,2,13]],"date-time":"2023-02-13T00:00:00Z","timestamp":1676246400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2023,3,13]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We demonstrate that lithium hexamethyldisilazide (LiHMDS) acts as an effective base for deprotonative coupling reactions of toluenes with ketones to afford stilbenes. Various functionalities (halogen, OCF<jats:sub>3<\/jats:sub>, amide, Me, aryl, alkenyl, alkynyl, SMe, and SPh) are allowed on the toluenes. Notably, this system proved successful with low\u2010reactive toluenes bearing a large pKa value compared to that of the conjugate acid of LiHMDS (hexamethyldisilazane, 25.8, THF), as demonstrated by 4\u2010phenyltoluene (38.57, THF) and toluene itself (\u223c43, DMSO).<\/jats:p>","DOI":"10.1002\/chem.202203549","type":"journal-article","created":{"date-parts":[[2022,12,7]],"date-time":"2022-12-07T10:45:41Z","timestamp":1670409941000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["LiHMDS\u2010Mediated Deprotonative Coupling of Toluenes with Ketones"],"prefix":"10.1002","volume":"29","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9640-8283","authenticated-orcid":false,"given":"Masanori","family":"Shigeno","sequence":"first","affiliation":[{"name":"Department of Biophysical Chemistry Graduate School of Pharmaceutical Science Tohoku University  6-3 Aoba Sendai 980-8578 Japan"},{"name":"JST, PRESTO  Kawaguchi Saitama 332-0012 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Akihisa","family":"Kajima","sequence":"additional","affiliation":[{"name":"Department of Biophysical Chemistry Graduate School of Pharmaceutical Science Tohoku University  6-3 Aoba Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eito","family":"Toyama","sequence":"additional","affiliation":[{"name":"Department of Biophysical Chemistry Graduate School of Pharmaceutical Science Tohoku University  6-3 Aoba Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Toshinobu","family":"Korenaga","sequence":"additional","affiliation":[{"name":"Department of Chemistry and Biological Sciences Faculty of Science and Engineering Iwate University Ueda  Morioka 020-8551 Japan"},{"name":"Soft-Path Science and Engineering Research Center (SPERC) Iwate University  Ueda Morioka 020-8551 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroyuki","family":"Yamakoshi","sequence":"additional","affiliation":[{"name":"Central Analytical Center Graduate School of Pharmaceutical Science, Tohoku University  6-3 Aoba Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kanako","family":"Nozawa\u2010Kumada","sequence":"additional","affiliation":[{"name":"Department of Biophysical Chemistry Graduate School of Pharmaceutical Science Tohoku University  6-3 Aoba Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yoshinori","family":"Kondo","sequence":"additional","affiliation":[{"name":"Department of Biophysical Chemistry Graduate School of Pharmaceutical Science Tohoku University  6-3 Aoba Sendai 980-8578 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,2,13]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"For reviews 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See:"},{"key":"e_1_2_7_28_2","first-page":"1","volume":"47","author":"Clark R. D.","year":"1995","journal-title":"Org. React."},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(98)83011-1"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1099-0682(200006)2000:6<1115::AID-EJIC1115>3.3.CO;2-B"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja110234v"},{"key":"e_1_2_7_32_1","unstructured":"\u00a0"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b03287"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710128"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611374"},{"key":"e_1_2_7_36_1","unstructured":"\u00a0"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b01542"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b03108"},{"key":"e_1_2_7_39_1","unstructured":"\u00a0"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201713165"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.5b03384"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01994"},{"key":"e_1_2_7_43_1","unstructured":"For reviews see:"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9OB02495F"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/D1CC06328F"},{"key":"e_1_2_7_46_1","unstructured":"\u00a0"},{"key":"e_1_2_7_47_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-05638-y"},{"key":"e_1_2_7_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02737"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c02890"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c02446"},{"key":"e_1_2_7_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19670500318"},{"key":"e_1_2_7_52_2","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19690520836"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201904658"},{"key":"e_1_2_7_54_1","unstructured":"\u00a0"},{"key":"e_1_2_7_55_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711291"},{"key":"e_1_2_7_56_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1610378"},{"key":"e_1_2_7_57_2","doi-asserted-by":"publisher","DOI":"10.1038\/s42004-021-00459-5"},{"key":"e_1_2_7_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01608a012"},{"key":"e_1_2_7_59_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja994432p"},{"key":"e_1_2_7_60_1","unstructured":"For the palladium-catalyzed reactions of toluenes with arylhalides in the presence of KHMDS see:"},{"key":"e_1_2_7_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b05143"},{"key":"e_1_2_7_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b08863"},{"key":"e_1_2_7_63_1","first-page":"3225","author":"Monsieurs K.","year":"2006","journal-title":"Synlett"},{"key":"e_1_2_7_64_1","unstructured":"\u00a0"},{"key":"e_1_2_7_65_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB02007A"},{"key":"e_1_2_7_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b00550"},{"key":"e_1_2_7_67_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201901501"},{"key":"e_1_2_7_68_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.oprd.8b00247"},{"key":"e_1_2_7_69_2","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.c19-00589"},{"key":"e_1_2_7_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.201800438"},{"key":"e_1_2_7_71_1","unstructured":"As related studies we also reported the deprotonative carboxylations of benzylic C\u2013H bonds using a combined Br\u00f8nsted base (LiO-t-Bu\/CsF). See:"},{"key":"e_1_2_7_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.2c01986"},{"key":"e_1_2_7_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b01386"},{"key":"e_1_2_7_74_1","volume-title":"Stilbenes: Applications in Chemistry, Life Sciences and Materials Science","author":"Likhtenshtein G.","year":"2010"},{"key":"e_1_2_7_75_1","unstructured":"The effects of bases were also examined in the reaction of1\u2009hand2\u2009b(Figure\u20053) showing the high reactivity of LiHMDS (Table\u2005S1)."},{"key":"e_1_2_7_76_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00310a038"},{"key":"e_1_2_7_77_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00217a050"},{"key":"e_1_2_7_78_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00156a004"},{"key":"e_1_2_7_79_1","unstructured":"The formation of alcohol productC and not that of the amine product through the imine intermediate similar to the reaction reported by Walsh Mao and coworkers (Figure\u20051a Equation\u2005(1)) [12a 12b]was confirmed as follows: When the reaction mixture of1\u2009aand2\u2009awas treated with MeI methyl ether product4was obtained in 74\u2009% yield (Scheme\u2005S2)."},{"key":"e_1_2_7_80_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00217a023"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203549","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/chem.202203549","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202203549","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T17:41:52Z","timestamp":1760290912000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202203549"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,2,13]]},"references-count":80,"journal-issue":{"issue":"15","published-print":{"date-parts":[[2023,3,13]]}},"alternative-id":["10.1002\/chem.202203549"],"URL":"https:\/\/doi.org\/10.1002\/chem.202203549","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,2,13]]},"assertion":[{"value":"2022-11-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-02-13","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202203549"}}