{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T06:35:37Z","timestamp":1775198137336,"version":"3.50.1"},"reference-count":61,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2019,9,26]],"date-time":"2019-09-26T00:00:00Z","timestamp":1569456000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["The Chemical Record"],"published-print":{"date-parts":[[2020,5]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>A transition metal catalyzed alkylation with an alkyl halide is one of the most difficult reactions to achieve, because of the difficult oxidative addition of an alkyl\u2010halogen bond to a metal, and the tendency of the resulting alkylmetal intermediate to undergo a \u03b2\u2010hydride elimination reaction to give an olefin. In this review, we discuss hybrid reaction systems involving Cu catalyzed combination of radicals and organometallic species, which enable facile alkylation reactions to construct C\u2212C and C\u2010heteroatom bonds. This paper highlights recent progress in arylation, alkenylation, alkynylation, cyclization, addition and introduction of heteroatoms via these hybrid reaction systems.<\/jats:p>","DOI":"10.1002\/tcr.201900053","type":"journal-article","created":{"date-parts":[[2019,9,26]],"date-time":"2019-09-26T09:09:48Z","timestamp":1569488988000},"page":"403-412","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Hybrid Reaction Systems for the Synthesis of Alkylated Compounds Based upon Cu\u2010Catalyzed Coupling of Radicals and Organometallic Species"],"prefix":"10.1002","volume":"20","author":[{"given":"Kentaro","family":"Takeuchi","sequence":"first","affiliation":[{"name":"Graduate School of Science and Engineering Yamaguchi University  2-16-1 Tokiwadai Ube, Yamaguchi 755-8611 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yumi","family":"Murata","sequence":"additional","affiliation":[{"name":"Graduate School of Science and Engineering Yamaguchi University  2-16-1 Tokiwadai Ube, Yamaguchi 755-8611 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Goki","family":"Hirata","sequence":"additional","affiliation":[{"name":"Graduate School of Science and Engineering Yamaguchi University  2-16-1 Tokiwadai Ube, Yamaguchi 755-8611 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tom D.","family":"Sheppard","sequence":"additional","affiliation":[{"name":"Department of Chemistry University College London Christopher Ingold Laboratories  20 Gordon Street London WC1H 0AJ U.K."}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2659-4826","authenticated-orcid":false,"given":"Takashi","family":"Nishikata","sequence":"additional","affiliation":[{"name":"Graduate School of Science and Engineering Yamaguchi University  2-16-1 Tokiwadai Ube, Yamaguchi 755-8611 Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2019,9,26]]},"reference":[{"key":"e_1_2_7_1_1","unstructured":"\u00a0"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(95)00434-A"},{"key":"e_1_2_7_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.10026"},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200802415"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.8b00265"},{"key":"e_1_2_7_6_1","unstructured":"\u00a0"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo01096a625"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01536a062"},{"key":"e_1_2_7_9_1","unstructured":"For reviews see:"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-1972-21818"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20011001)40:19<3567::AID-ANIE3567>3.0.CO;2-C"},{"key":"e_1_2_7_11_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20011001)113:19<3679::AID-ANGE3679>3.0.CO;2-I"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)01172-3"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201807623"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201807623"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b03387"},{"key":"e_1_2_7_15_1","unstructured":"\u00a0"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108350"},{"key":"e_1_2_7_16_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108350"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja409661n"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b03287"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b03591"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0037-1611659"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b01572"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja038177r"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.7b02615"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201700798"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms11676"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc36554e"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201813425"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201813425"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201706293"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201706293"},{"key":"e_1_2_7_28_3","doi-asserted-by":"publisher","DOI":"10.1126\/science.aad8313"},{"key":"e_1_2_7_29_1","unstructured":"\u00a0"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC02910A"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2018.11.048"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja411912p"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC00238A"},{"key":"e_1_2_7_34_1","unstructured":"\u00a0"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja510093x"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CC09393C"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/ol500224e"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr500706a"},{"key":"e_1_2_7_39_1","unstructured":"\u00a0"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201603426"},{"key":"e_1_2_7_40_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201603426"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1246\/cl.170062"},{"key":"e_1_2_7_42_1","first-page":"14222","volume":"136","author":"Xue W.","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"e_1_2_7_43_1","unstructured":"\u00a0"},{"key":"e_1_2_7_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7OB01831B"},{"key":"e_1_2_7_45_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b00940"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4OB00215F"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.6b02065"},{"key":"e_1_2_7_48_1","unstructured":"\u00a0"},{"key":"e_1_2_7_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/asia.201800630"},{"key":"e_1_2_7_50_2","doi-asserted-by":"publisher","DOI":"10.1002\/tcr.201800053"},{"key":"e_1_2_7_51_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02929"},{"key":"e_1_2_7_52_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b02735"},{"key":"e_1_2_7_53_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.8b02073"},{"key":"e_1_2_7_54_1","unstructured":"The hybrid concept can also be seen in a recent review. See Ref. [8]."}],"container-title":["The Chemical Record"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Ftcr.201900053","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tcr.201900053","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/tcr.201900053","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/tcr.201900053","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,6]],"date-time":"2023-09-06T13:34:44Z","timestamp":1694007284000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/tcr.201900053"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,9,26]]},"references-count":61,"journal-issue":{"issue":"5","published-print":{"date-parts":[[2020,5]]}},"alternative-id":["10.1002\/tcr.201900053"],"URL":"https:\/\/doi.org\/10.1002\/tcr.201900053","archive":["Portico"],"relation":{},"ISSN":["1527-8999","1528-0691"],"issn-type":[{"value":"1527-8999","type":"print"},{"value":"1528-0691","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,9,26]]},"assertion":[{"value":"2019-07-11","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-09-13","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2019-09-26","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}