{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,4]],"date-time":"2026-09-04T03:38:06Z","timestamp":1788493086872,"version":"build-2803163510"},"reference-count":84,"publisher":"Wiley","issue":"46","license":[{"start":{"date-parts":[[2012,9,27]],"date-time":"2012-09-27T00:00:00Z","timestamp":1348704000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2012,11,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Regio\u2010 and stereoselective installation of boryl and stannyl moieties into a carbon\u2013carbon triple bond of various alkynes has been achieved based on a three\u2010component coupling reaction by using a diboron and a tin alkoxide with the aid of a copper(II) acetate\u2013tricyclohexylphosphine complex, giving diverse\n                    <jats:italic>vic<\/jats:italic>\n                    \u2010borylstannylalkenes in a straightforward manner. Carbon\u2013tin and carbon\u2013boron bonds of the resulting borylstannylation product are successively transformed into carbon\u2013carbon bonds by a Migita\u2013Kosugi\u2013Stille and a Suzuki\u2013Miyaura coupling, leading to the formation of (\n                    <jats:italic>Z<\/jats:italic>\n                    )\u2010tamoxifen with anti\u2010breast cancer activity.\n                  <\/jats:p>","DOI":"10.1002\/chem.201202435","type":"journal-article","created":{"date-parts":[[2012,9,27]],"date-time":"2012-09-27T14:20:08Z","timestamp":1348755608000},"page":"14841-14844","source":"Crossref","is-referenced-by-count":82,"title":["Copper\u2010Catalyzed Three\u2010Component Borylstannylation of Alkynes"],"prefix":"10.1002","volume":"18","author":[{"given":"Yuki","family":"Takemoto","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hiroto","family":"Yoshida","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ken","family":"Takaki","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,9,27]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"For reviews see:"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9902594"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr9902805"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr050530j"},{"key":"e_1_2_6_5_2","unstructured":"For Si and Sn see:"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00369a001"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00231a009"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1021\/om00034a072"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-2004-822405"},{"key":"e_1_2_6_10_2","unstructured":"For B and Si see:"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1039\/cc9960002777"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1039\/a702802d"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00444-5"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.82.29"},{"key":"e_1_2_6_15_2","unstructured":"For B and Sn see:"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/om9607199"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/om000042w"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol100824f"},{"key":"e_1_2_6_19_2","volume-title":"Metal\u2010Catalyzed Cross\u2010Coupling Reactions","year":"2004"},{"key":"e_1_2_6_20_2","unstructured":"\u00a0"},{"key":"e_1_2_6_21_2","doi-asserted-by":"publisher","DOI":"10.2174\/0929867301666220210212635"},{"key":"e_1_2_6_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm020450x"},{"key":"e_1_2_6_23_2","unstructured":"\u00a0"},{"key":"e_1_2_6_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00351a010"},{"key":"e_1_2_6_25_2","doi-asserted-by":"publisher","DOI":"10.1200\/JCO.2002.10.057"},{"key":"e_1_2_6_26_2","unstructured":"\u00a0"},{"key":"e_1_2_6_27_2","doi-asserted-by":"publisher","DOI":"10.1023\/B:BREA.0000003957.54851.11"},{"key":"e_1_2_6_28_2","doi-asserted-by":"publisher","DOI":"10.1007\/s10549-004-4384-z"},{"key":"e_1_2_6_29_2","unstructured":"For the synthesis ofgem\u2010dimetallated alkenes by insertion reactions of carbenoids into metal\u2013metal bonds see:"},{"key":"e_1_2_6_30_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20010216)113:4<812::AID-ANGE8120>3.0.CO;2-O"},{"key":"e_1_2_6_30_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20010216)40:4<790::AID-ANIE7900>3.0.CO;2-T"},{"key":"e_1_2_6_31_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(02)00648-8"},{"key":"e_1_2_6_32_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106706"},{"key":"e_1_2_6_32_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106706"},{"key":"e_1_2_6_33_2","unstructured":"For recent examples on Cu\u2010catalyzed reactions by using a diboron see:"},{"key":"e_1_2_6_34_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200802342"},{"key":"e_1_2_6_34_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200802342"},{"key":"e_1_2_6_35_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200901879"},{"key":"e_1_2_6_35_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200901879"},{"key":"e_1_2_6_36_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo101024f"},{"key":"e_1_2_6_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101793a"},{"key":"e_1_2_6_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja103783p"},{"key":"e_1_2_6_39_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201106299"},{"key":"e_1_2_6_39_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201106299"},{"key":"e_1_2_6_40_2","unstructured":"For reactions of alkenyl\u2013 or aryl\u2013copper species with carbon electrophiles see:"},{"key":"e_1_2_6_41_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol800829q"},{"key":"e_1_2_6_42_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200801857"},{"key":"e_1_2_6_42_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801857"},{"key":"e_1_2_6_43_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201008007"},{"key":"e_1_2_6_43_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201008007"},{"key":"e_1_2_6_44_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201006292"},{"key":"e_1_2_6_44_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201006292"},{"key":"e_1_2_6_45_2","unstructured":"To date \u03b2\u2010borylalkenyl\u2013copper intermediates have been captured by protons in the Cu\u2010catalyzed borylations of alkynes with a diboron to give hydroboration products except for \u03b2\u2010oxygen elimination (in the synthesis of allenylboranes) and capture by boron (in the diborylation); for the Cu\u2010catalyzed hydroboration of alkynes see:"},{"key":"e_1_2_6_46_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0022-328X(00)00826-3"},{"key":"e_1_2_6_47_2","doi-asserted-by":"publisher","DOI":"10.1039\/B716697D"},{"key":"e_1_2_6_48_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja9089928"},{"key":"e_1_2_6_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/B919515G"},{"key":"e_1_2_6_50_2","doi-asserted-by":"publisher","DOI":"10.1039\/C0CC04496B"},{"key":"e_1_2_6_51_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201007182"},{"key":"e_1_2_6_51_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201007182"},{"key":"e_1_2_6_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja806602h"},{"key":"e_1_2_6_53_2","unstructured":"The palladium\u2010catalyzed borylstannylation of alkyl(aryl)alkynes generally produces a mixture of regioisomers which is in contrast to the results described herein; see refs. [4a \u2009c]."},{"key":"e_1_2_6_54_2","unstructured":"The observed regioselectivity in the reaction of alkyl(aryl)alkynes is ascribable to the exclusive generation ofgem\u2010(aryl)alkenyl\u2013copper species (7 R=Ar Scheme\u20051) induced by the electronic directing effect of the aryl moieties."},{"key":"e_1_2_6_55_2","unstructured":"\u00a0"},{"key":"e_1_2_6_56_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja2007643"},{"key":"e_1_2_6_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103612"},{"key":"e_1_2_6_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/om700999w"},{"key":"e_1_2_6_59_2","unstructured":"\u00a0"},{"key":"e_1_2_6_60_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol101171v"},{"key":"e_1_2_6_61_2","doi-asserted-by":"publisher","DOI":"10.1039\/c0cc01635g"},{"key":"e_1_2_6_62_2","unstructured":"The present borylstannylation does not proceed through diborylation and subsequent transformation of a C\uf8ffB bond of a diborylalkene into a C\uf8ffSn bond because the Cu\u2010catalyzed diborylation of alkynes was found not to occur at room temperature."},{"key":"e_1_2_6_63_2","unstructured":"No traces of distannylated alkenes were observed in the present reaction which shows that the borylstannylation products do not undergo this boron to tin transformation probably because of the steric bulk of the stannyl moieties."},{"key":"e_1_2_6_64_2","unstructured":"Formation of a silyl copper species by \u03c3\u2010bond metathesis between a copper alkoxide and a borylsilane has been reported; see:"},{"key":"e_1_2_6_65_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja910989n"},{"key":"e_1_2_6_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol200509c"},{"key":"e_1_2_6_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja109464u"},{"key":"e_1_2_6_68_2","unstructured":"The steric hindrance of3\u2009cdoes not inhibit the interaction of3\u2009cwith7 which is in contrast to the case with6. At present the exact reason for the different reactivity of3\u2009ctoward6or7is unclear."},{"key":"e_1_2_6_69_2","unstructured":"For representative examples on the synthesis of (Z)\u2010tamoxifen see:"},{"key":"e_1_2_6_70_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja037566i"},{"key":"e_1_2_6_71_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja054484g"},{"key":"e_1_2_6_72_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja075234y"},{"key":"e_1_2_6_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol902278q"},{"key":"e_1_2_6_74_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201108211"},{"key":"e_1_2_6_74_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201108211"}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fchem.201202435","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.201202435","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T09:00:53Z","timestamp":1760259653000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.201202435"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,9,27]]},"references-count":84,"journal-issue":{"issue":"46","published-print":{"date-parts":[[2012,11,12]]}},"alternative-id":["10.1002\/chem.201202435"],"URL":"https:\/\/doi.org\/10.1002\/chem.201202435","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,9,27]]}}}