{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,20]],"date-time":"2026-10-20T07:47:53Z","timestamp":1792482473914,"version":"4.5.0"},"reference-count":89,"publisher":"Wiley","issue":"35","license":[{"start":{"date-parts":[[2018,8,2]],"date-time":"2018-08-02T00:00:00Z","timestamp":1533168000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100000266","name":"Engineering and Physical Sciences Research Council","doi-asserted-by":"publisher","award":["EP\/P002951\/1"],"award-info":[{"award-number":["EP\/P002951\/1"]}],"id":[{"id":"10.13039\/501100000266","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Angew Chem Int Ed"],"published-print":{"date-parts":[[2018,8,27]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    A form independent activation of zinc, concomitant generation of organozinc species and engagement in a Negishi cross\u2010coupling reaction via mechanochemical methods is reported. The reported method exhibits a broad substrate scope for both C(sp\n                    <jats:sup>3<\/jats:sup>\n                    )\u2013C(sp\n                    <jats:sup>2<\/jats:sup>\n                    ) and C(sp\n                    <jats:sup>2<\/jats:sup>\n                    )\u2013C(sp\n                    <jats:sup>2<\/jats:sup>\n                    ) couplings and is tolerant to many important functional groups. The method may offer broad reaching opportunities for the in\u2005situ generation organometallic compounds from base metals and their concomitant engagement in synthetic reactions via mechanochemical methods.\n                  <\/jats:p>","DOI":"10.1002\/anie.201806480","type":"journal-article","created":{"date-parts":[[2018,7,17]],"date-time":"2018-07-17T07:14:30Z","timestamp":1531811670000},"page":"11339-11343","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":167,"title":["Mechanochemical Activation of Zinc and Application to Negishi Cross\u2010Coupling"],"prefix":"10.1002","volume":"57","author":[{"given":"Qun","family":"Cao","sequence":"first","affiliation":[{"name":"School of Chemistry Cardiff University  Main Building, Park Place Cardiff CF10 3EQ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joseph L.","family":"Howard","sequence":"additional","affiliation":[{"name":"School of Chemistry Cardiff University  Main Building, Park Place Cardiff CF10 3EQ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Emilie","family":"Wheatley","sequence":"additional","affiliation":[{"name":"School of Chemistry Cardiff University  Main Building, Park Place Cardiff CF10 3EQ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8604-229X","authenticated-orcid":false,"given":"Duncan L.","family":"Browne","sequence":"additional","affiliation":[{"name":"School of Chemistry Cardiff University  Main Building, Park Place Cardiff CF10 3EQ UK"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,8,2]]},"reference":[{"key":"e_1_2_2_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.8b02266"},{"key":"e_1_2_2_1_2","doi-asserted-by":"crossref","unstructured":"Isr. J. Chem.2018 58 1.","DOI":"10.1002\/ijch.201880101"},{"key":"e_1_2_2_2_1","unstructured":"For some recent reviews on mechanochemistry see:"},{"key":"e_1_2_2_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC05371A"},{"key":"e_1_2_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7GC03797J"},{"key":"e_1_2_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscentsci.6b00277"},{"key":"e_1_2_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.6b02887"},{"key":"e_1_2_2_7_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.14.81"},{"key":"e_1_2_2_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/acssuschemeng.7b03260"},{"key":"e_1_2_2_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/C1CS15171A"},{"key":"e_1_2_2_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00628G"},{"key":"e_1_2_2_11_1","unstructured":"\u00a0"},{"key":"e_1_2_2_12_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0036-1588843"},{"key":"e_1_2_2_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201204526"},{"key":"e_1_2_2_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201204526"},{"key":"e_1_2_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201309841"},{"key":"e_1_2_2_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201309841"},{"key":"e_1_2_2_15_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201700216"},{"key":"e_1_2_2_15_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201700216"},{"key":"e_1_2_2_16_1","unstructured":"\u00a0"},{"key":"e_1_2_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0605265"},{"key":"e_1_2_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja908198d"},{"key":"e_1_2_2_19_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0913307107"},{"key":"e_1_2_2_20_1","unstructured":"\u00a0"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200701984"},{"key":"e_1_2_2_21_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200701984"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol400242r"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b03270"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201403015"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201704400"},{"key":"e_1_2_2_25_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201704400"},{"key":"e_1_2_2_26_1","unstructured":"\u00a0"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)98708-2"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00036a060"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200900575"},{"key":"e_1_2_2_30_1","unstructured":"\u00a0"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3973000269b"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00334a056"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00004a021"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9844478"},{"key":"e_1_2_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo952104b"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00148a033"},{"key":"e_1_2_2_37_1","unstructured":"For some examples of preparing activated zinc using chemical additives see:"},{"key":"e_1_2_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00245a057"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00259a038"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80190-8"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)81242-9"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00230a029"},{"key":"e_1_2_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo026746s"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01261a033"},{"key":"e_1_2_2_45_2","doi-asserted-by":"publisher","DOI":"10.1039\/c39840000086"},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0272693"},{"key":"e_1_2_2_47_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2003.12.119"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00013a055"},{"key":"e_1_2_2_49_1","unstructured":"\u00a0"},{"key":"e_1_2_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00046a026"},{"key":"e_1_2_2_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601450"},{"key":"e_1_2_2_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601450"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja071380s"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol7030697"},{"key":"e_1_2_2_54_1","unstructured":"The exact identity of the formed organozinc species has not been confirmed however given the ease of handling and low exotherms upon quenching (such as those studied and shown in Scheme\u20052 and Table\u2005S2) we suspect that the materials are monoalkylzinc halides rather than dialkylzinc species."},{"key":"e_1_2_2_55_1","unstructured":"For some previous examples of 1-pot multi-step mechanochemical reactions see:"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.3762\/bjoc.13.189"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2013.06.018"},{"key":"e_1_2_2_58_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4SC01252F"},{"key":"e_1_2_2_59_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6RA03222B"},{"key":"e_1_2_2_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b09011"},{"key":"e_1_2_2_61_1","unstructured":"For pioneering developments of the Pd-PEPPSI catalyst series see:"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200601663"},{"key":"e_1_2_2_62_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200601663"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106131"},{"key":"e_1_2_2_63_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106131"},{"key":"e_1_2_2_64_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201000359"},{"key":"e_1_2_2_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200906811"},{"key":"e_1_2_2_65_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200906811"},{"key":"e_1_2_2_66_1","unstructured":"Organ and co-workers investigated the effect of salt additives on Negishi coupling reactions and found that the addition of salts for example lithium or tertrabutyl ammonium could facilitate the formation of higher-order zincates which are more active transmetallating agents for Negishi coupling. TBAB (tetrabutylammonium bromide) was chosen as salt additive in preference to hydroscopic lithium salts. For the effect of salts as additives on palladium catalyzed Negishi coupling see:"},{"key":"e_1_2_2_67_2","doi-asserted-by":"publisher","DOI":"10.1039\/c002759f"},{"key":"e_1_2_2_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201101029"},{"key":"e_1_2_2_69_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201203547"},{"key":"e_1_2_2_69_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201203547"},{"key":"e_1_2_2_70_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201400459"},{"key":"e_1_2_2_70_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201400459"},{"key":"e_1_2_2_71_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00931"},{"key":"e_1_2_2_72_1","unstructured":"See supporting information for further information on reaction optimisation and preparing organozinc species."},{"key":"e_1_2_2_73_1","unstructured":"For other examples of operationally simple Barbier\u2013Negishi reactions see:"},{"key":"e_1_2_2_74_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja906803t"},{"key":"e_1_2_2_75_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201711990"},{"key":"e_1_2_2_75_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201711990"},{"key":"e_1_2_2_76_1","unstructured":"You may find mills in laboratories concerned with formulation science forensic science geology earth science and food science\u2014there is likely to be access to a mill already in your institute company or university."}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201806480","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201806480","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,14]],"date-time":"2023-09-14T19:52:34Z","timestamp":1694721154000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201806480"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,8,2]]},"references-count":89,"journal-issue":{"issue":"35","published-print":{"date-parts":[[2018,8,27]]}},"alternative-id":["10.1002\/anie.201806480"],"URL":"https:\/\/doi.org\/10.1002\/anie.201806480","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,8,2]]},"assertion":[{"value":"2018-06-05","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-08-02","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}