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Iodides"],"prefix":"10.1002","volume":"57","author":[{"given":"Keisho","family":"Okura","sequence":"first","affiliation":[{"name":"Department of Chemistry Graduate School of Science Kyoto University  Sakyo-ku Kyoto 606-8502 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tsuyoshi","family":"Teranishi","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry for Environment School of Science and Technology Kwansei Gakuin University  Sanda Hyogo 669-1337 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yuto","family":"Yoshida","sequence":"additional","affiliation":[{"name":"Department of Chemistry Graduate School of Science Kyoto University  Sakyo-ku Kyoto 606-8502 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8564-984X","authenticated-orcid":false,"given":"Eiji","family":"Shirakawa","sequence":"additional","affiliation":[{"name":"Department of Applied Chemistry for Environment School of Science and Technology Kwansei Gakuin University  Sanda Hyogo 669-1337 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2018,5,16]]},"reference":[{"key":"e_1_2_2_1_1","unstructured":"Reviews:"},{"key":"e_1_2_2_2_2","volume-title":"Metal-Catalyzed Cross-Coupling Reactions and more, 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catalysis."},{"key":"e_1_2_2_20_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200905824"},{"key":"e_1_2_2_20_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200905824"},{"key":"e_1_2_2_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja309578k"},{"key":"e_1_2_2_22_2","doi-asserted-by":"publisher","DOI":"10.1002\/adsc.201200416"},{"key":"e_1_2_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo3018878"},{"key":"e_1_2_2_24_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201300829"},{"key":"e_1_2_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201402487"},{"key":"e_1_2_2_26_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC00384A"},{"key":"e_1_2_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja507675f"},{"key":"e_1_2_2_28_2","doi-asserted-by":"publisher","DOI":"10.1039\/C6QO00109B"},{"key":"e_1_2_2_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b01376"},{"key":"e_1_2_2_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC04521E"},{"key":"e_1_2_2_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.6b02553"},{"key":"e_1_2_2_32_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b05436"},{"key":"e_1_2_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b11813"},{"key":"e_1_2_2_34_2","doi-asserted-by":"publisher","DOI":"10.1039\/C8SC00008E"},{"key":"e_1_2_2_35_1","unstructured":"Reviews on \u201celectron catalysis\u201d:"},{"key":"e_1_2_2_36_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchem.2031"},{"key":"e_1_2_2_37_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201505090"},{"key":"e_1_2_2_37_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201505090"},{"key":"e_1_2_2_38_1","unstructured":"The transition-metal-free coupling of arylboronic acids with allylic propargylic and benzylic halides has been reported where a non-radical mechanism is proposed:"},{"key":"e_1_2_2_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201101527"},{"key":"e_1_2_2_40_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0031-1290656"},{"key":"e_1_2_2_41_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0033-1339199"},{"key":"e_1_2_2_42_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2016.07.089"},{"key":"e_1_2_2_43_1","unstructured":"Aryl(ethyl)zinc reagents prepared from arylboronic acids and diethylzinc have often been used for the asymmetric arylation of aldehydes. The first example:"},{"key":"e_1_2_2_44_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja028518l"},{"key":"e_1_2_2_45_2","first-page":"454","volume":"35","author":"Schmidt F.","year":"2006","journal-title":"Chem. Soc. Rev."},{"key":"e_1_2_2_46_2","doi-asserted-by":"publisher","DOI":"10.1590\/S0103-50532008000500003"},{"key":"e_1_2_2_47_1","unstructured":"A mechanistic study on transmetalation between boron and zinc:"},{"key":"e_1_2_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200703103"},{"key":"e_1_2_2_48_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200703103"},{"key":"e_1_2_2_49_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201202219"},{"key":"e_1_2_2_49_3","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201202219"},{"key":"e_1_2_2_50_1","doi-asserted-by":"publisher","DOI":"10.3987\/COM-02-9464"},{"key":"e_1_2_2_51_1","unstructured":"ZnCl2(99.999\u2009% trace metals basis Sigma\u2013Aldrich Co. product number 229997) and KOt-Bu (99.99\u2009% trace metals basis Sigma\u2013Aldrich Co. product number 659878) were used in all entries in Table\u20052. The reaction using ZnCl2and KOt-Bu purchased from a different supplier (Wako Pure Chemical Industries) under the conditions of entry\u20055 produced a comparable yield (96\u2009%) of3\u2009aawith a full conversion of2\u2009a. For the details see the Supporting Information. In addition to this result the outcome that no coupling took place when using K3PO4or K2CO3instead of KOt-Bu (entries\u20056 and 7 of Table\u20052) excludes the possibility that the present cross-coupling is catalyzed by a trace amount of a transition metal such as palladium contained in the reagents since K3PO4and K2CO3are known to be effective bases for the palladium-catalyzed Suzuki\u2013Miyaura coupling. For a recent example of a Suzuki\u2013Miyaura coupling that was initially considered to be transition-metal-free but later was revealed to be catalyzed by a trace amount of palladium contained in the reagents see:"},{"key":"e_1_2_2_52_2","doi-asserted-by":"publisher","DOI":"10.1039\/c2cc17401d"},{"key":"e_1_2_2_53_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2012.04.043"},{"key":"e_1_2_2_54_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja5101036"},{"key":"e_1_2_2_55_1","unstructured":"No involvement of aryl radical species is supported by a radical clock experiment using 2-(3-butenyl)phenyl iodide (2\u2009h) which is often used for a radical clock reaction the radical derived from which is known to readily cyclize (kc=5\u00d710\u22128\u2005s\u22121at 50\u2009\u00b0C). The coupling of2\u2009hdid not give any cyclization product but the coupling product in a high yield (Table\u20053 entry\u20058). Radical clock reactions using2\u2009h:"},{"key":"e_1_2_2_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01048a075"},{"key":"e_1_2_2_57_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b02399"},{"key":"e_1_2_2_58_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo500222d"},{"key":"e_1_2_2_59_1","unstructured":"Cation radical [Ar1\u2013Y].+ which is generated by SET in the initiation step reacts with another Ar1\u2013Y to give [Ar1\u2013Ar1].\u2212 from which SET to I\u2013Ar2takes place to give Ar1\u2013Ar1and [I\u2013Ar2].\u2212. Actually a small amount of Ar1\u2013Ar1derived from an arylboroxine (4) is observed in each reaction. For example the coupling reaction of phenylboroxine (4\u2009a) with 4-iodoanisole (2\u2009a) gave biphenyl in 1.1\u2009% yield based on2\u2009a(Table\u20052 entry\u20055). See also Refs.\u2005[3b] and [4b]."},{"key":"e_1_2_2_60_1","unstructured":"Bromo- or chloro-substituted iodobenzenes are often used to probe the involvement of radical anion intermediates in SRN1 reactions where bissubstitution predominantly takes place:"},{"key":"e_1_2_2_61_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00938a044"},{"key":"e_1_2_2_62_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00938a045"},{"key":"e_1_2_2_63_2","doi-asserted-by":"publisher","DOI":"10.1039\/C7SC00100B"}],"container-title":["Angewandte Chemie International Edition"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fanie.201802813","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/anie.201802813","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,9,18]],"date-time":"2023-09-18T13:54:16Z","timestamp":1695045256000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/anie.201802813"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,5,16]]},"references-count":70,"journal-issue":{"issue":"24","published-print":{"date-parts":[[2018,6,11]]}},"alternative-id":["10.1002\/anie.201802813"],"URL":"https:\/\/doi.org\/10.1002\/anie.201802813","archive":["Portico"],"relation":{},"ISSN":["1433-7851","1521-3773"],"issn-type":[{"value":"1433-7851","type":"print"},{"value":"1521-3773","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,5,16]]},"assertion":[{"value":"2018-03-07","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-05-16","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}