{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,13]],"date-time":"2026-10-13T03:53:27Z","timestamp":1791863607844,"version":"4.3.4"},"reference-count":101,"publisher":"American Association for the Advancement of Science (AAAS)","issue":"6538","funder":[{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE-1654122"],"award-info":[{"award-number":["CHE-1654122"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008982","name":"National Science Foundation","doi-asserted-by":"publisher","award":["CHE-1654122"],"award-info":[{"award-number":["CHE-1654122"]}],"id":[{"id":"10.13039\/501100008982","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Science"],"published-print":{"date-parts":[[2021,4,9]]},"abstract":"<jats:title>Slipping boron into alkyl ethers<\/jats:title>\n                  <jats:p>\n                    The carbon\u2013oxygen bonds that hold alkyl ethers together are relatively inert. Lyu\n                    <jats:italic>et al.<\/jats:italic>\n                    report that zinc and nickel can team up to insert boron between the carbon and oxygen using an unusual mechanism. First, a dibromoborane pries open the bond with help from a zinc ion. Next, the nickel stitches together the carbon and boron, and the oxidation of metallic zinc starts the cycle over again. Versatile reactivity at the inserted boron center can then add carbons to the original ether or swap out oxygen for nitrogen.\n                  <\/jats:p>\n                  <jats:p>\n                    <jats:italic>Science<\/jats:italic>\n                    , this issue p.\n                    <jats:related-article issue=\"6538\" page=\"175\" related-article-type=\"in-this-issue\" vol=\"372\">175<\/jats:related-article>\n                  <\/jats:p>","DOI":"10.1126\/science.abg5526","type":"journal-article","created":{"date-parts":[[2021,4,9]],"date-time":"2021-04-09T13:59:01Z","timestamp":1617976741000},"page":"175-182","source":"Crossref","is-referenced-by-count":225,"title":["Boron insertion into alkyl ether bonds via zinc\/nickel tandem catalysis"],"prefix":"10.1126","volume":"372","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-0476-0352","authenticated-orcid":true,"given":"Hairong","family":"Lyu","sequence":"first","affiliation":[{"name":"Department of Chemistry, University of Chicago, Chicago, IL 60637, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8133-4165","authenticated-orcid":true,"given":"Ilia","family":"Kevlishvili","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4100-8001","authenticated-orcid":true,"given":"Xuan","family":"Yu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Chicago, Chicago, IL 60637, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8188-632X","authenticated-orcid":true,"given":"Peng","family":"Liu","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1331-6015","authenticated-orcid":true,"given":"Guangbin","family":"Dong","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Chicago, Chicago, IL 60637, USA."}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"221","reference":[{"key":"e_1_3_2_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr068360d"},{"key":"e_1_3_2_3_2","unstructured":"C. Thebtaranonth Y. Thebtaranonth Cyclization Reaction (CRC Press ed. 1 1993)."},{"key":"e_1_3_2_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4CS00206G"},{"key":"e_1_3_2_5_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar500345f"},{"key":"e_1_3_2_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr100259t"},{"key":"e_1_3_2_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.accounts.5b00223"},{"key":"e_1_3_2_8_2","doi-asserted-by":"publisher","DOI":"10.1080\/00304949609356549"},{"key":"e_1_3_2_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00502a074"},{"key":"e_1_3_2_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja710944j"},{"key":"e_1_3_2_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja101186p"},{"key":"e_1_3_2_12_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1200437"},{"key":"e_1_3_2_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03955"},{"key":"e_1_3_2_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201511486"},{"key":"e_1_3_2_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b03253"},{"key":"e_1_3_2_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b07396"},{"key":"e_1_3_2_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b07567"},{"key":"e_1_3_2_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.6b10255"},{"key":"e_1_3_2_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00003a001"},{"key":"e_1_3_2_20_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9SC04069B"},{"key":"e_1_3_2_21_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.198404541"},{"key":"e_1_3_2_22_2","doi-asserted-by":"publisher","DOI":"10.4155\/fmc.09.71"},{"key":"e_1_3_2_23_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.9b01518"},{"key":"e_1_3_2_24_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biomac.9b01128"},{"key":"e_1_3_2_25_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201705153"},{"key":"e_1_3_2_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00561"},{"key":"e_1_3_2_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja075932i"},{"key":"e_1_3_2_28_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.organomet.8b00567"},{"key":"e_1_3_2_29_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.1253647"},{"key":"e_1_3_2_30_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0OB00880J"},{"key":"e_1_3_2_31_2","doi-asserted-by":"publisher","DOI":"10.1039\/C9CS00180H"},{"key":"e_1_3_2_32_2","doi-asserted-by":"publisher","DOI":"10.1038\/nature23265"},{"key":"e_1_3_2_33_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00345a074"},{"key":"e_1_3_2_34_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr00097a009"},{"key":"e_1_3_2_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00221a014"},{"key":"e_1_3_2_36_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200800201"},{"key":"e_1_3_2_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja048078t"},{"key":"e_1_3_2_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.7b01346"},{"key":"e_1_3_2_39_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja407589e"},{"key":"e_1_3_2_40_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-018-0669-y"},{"key":"e_1_3_2_41_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201501042"},{"key":"e_1_3_2_42_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.8b00628"},{"key":"e_1_3_2_43_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja055396z"},{"key":"e_1_3_2_44_2","doi-asserted-by":"publisher","DOI":"10.1039\/c3ra22905j"},{"key":"e_1_3_2_45_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201702331"},{"key":"e_1_3_2_46_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201500959"},{"key":"e_1_3_2_47_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.7b01835"},{"key":"e_1_3_2_48_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201712393"},{"key":"e_1_3_2_49_2","doi-asserted-by":"publisher","DOI":"10.1039\/B408760G"},{"key":"e_1_3_2_50_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802819p"},{"key":"e_1_3_2_51_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja012046d"},{"key":"e_1_3_2_52_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja809176m"},{"key":"e_1_3_2_53_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo5018537"},{"key":"e_1_3_2_54_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja105366u"},{"key":"e_1_3_2_55_2","doi-asserted-by":"publisher","DOI":"10.1021\/je9006794"},{"key":"e_1_3_2_56_2","doi-asserted-by":"publisher","DOI":"10.1002\/hc.520060206"},{"key":"e_1_3_2_57_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201004703"},{"key":"e_1_3_2_58_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol0350947"},{"key":"e_1_3_2_59_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(99)02096-1"},{"key":"e_1_3_2_60_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201506263"},{"key":"e_1_3_2_61_2","doi-asserted-by":"publisher","DOI":"10.1055\/s-0030-1260761"},{"key":"e_1_3_2_62_2","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201605648"},{"key":"e_1_3_2_63_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201405223"},{"key":"e_1_3_2_64_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(02)01606-4"},{"key":"e_1_3_2_65_2","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201805772"},{"key":"e_1_3_2_66_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0579210"},{"key":"e_1_3_2_67_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo00109a043"},{"key":"e_1_3_2_68_2","doi-asserted-by":"publisher","DOI":"10.1002\/cctc.201300182"},{"key":"e_1_3_2_69_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja509766f"},{"key":"e_1_3_2_70_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2008.12.033"},{"key":"e_1_3_2_71_2","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201900498"},{"key":"e_1_3_2_72_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.isci.2018.10.025"},{"key":"e_1_3_2_73_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0613761"},{"key":"e_1_3_2_74_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2005.02.033"},{"key":"e_1_3_2_75_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo0353177"},{"key":"e_1_3_2_76_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo030312v"},{"key":"e_1_3_2_77_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo802778z"},{"key":"e_1_3_2_78_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.9b02199"},{"key":"e_1_3_2_79_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm060639z"},{"key":"e_1_3_2_80_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol025973d"},{"key":"e_1_3_2_81_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2016.07.053"},{"key":"e_1_3_2_82_2","doi-asserted-by":"publisher","DOI":"10.1039\/C4RA10625C"},{"key":"e_1_3_2_83_2","doi-asserted-by":"publisher","DOI":"10.1039\/D0CC00903B"},{"key":"e_1_3_2_84_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja078137d"},{"key":"e_1_3_2_85_2","doi-asserted-by":"publisher","DOI":"10.1126\/science.aai8611"},{"key":"e_1_3_2_86_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo900504y"},{"key":"e_1_3_2_87_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035886e"},{"key":"e_1_3_2_88_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(97)10161-2"},{"key":"e_1_3_2_89_2","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c00282"},{"key":"e_1_3_2_90_2","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-018-06830-w"},{"key":"e_1_3_2_91_2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b01058"},{"key":"e_1_3_2_92_2","unstructured":"M. J. Frisch G. W. Trucks H. B. Schlegel G. E. Scuseria M. A. Robb J. R. Cheeseman G. Scalmani V. Barone G. A. Petersson H. Nakatsuji X. Li M. Caricato A. V. Marenich J. Bloino B. G. Janesko R. Gomperts B. Mennucci H. P. Hratchian J. V. Ortiz A. F. Izmaylov J. L. Sonnenberg D. Williams-Young F. Ding F. Lipparini F. Egidi J. Goings B. Peng A. Petrone T. Henderson D. Ranasinghe V. G. Zakrzewski J. Gao N. Rega G. Zheng W. Liang M. Hada M. Ehara K. Toyota R. Fukuda J. Hasegawa M. Ishida T. Nakajima Y. Honda O. Kitao H. Nakai T. Vreven K. Throssell J. A. Montgomery Jr. J. E. Peralta F. Ogliaro M. J. Bearpark J. J. Heyd E. N. Brothers K. N. Kudin V. N. Staroverov T. A. Keith R. Kobayashi J. Normand K. Raghavachari A. P. Rendell J. C. Burant S. S. Iyengar J. Tomasi M. Cossi J. M. Millam M. Klene C. Adamo R. Cammi J. W. Ochterski R. L. Martin K. Morokuma O. Farkas J. B. Foresman D. J. Fox Gaussian 16 Revision C.01 (Gaussian Inc. 2016)."},{"key":"e_1_3_2_93_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevB.37.785"},{"key":"e_1_3_2_94_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_3_2_95_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.3382344"},{"key":"e_1_3_2_96_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp810292n"},{"key":"e_1_3_2_97_2","doi-asserted-by":"publisher","DOI":"10.1007\/s00214-007-0310-x"},{"key":"e_1_3_2_98_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo970944f"},{"key":"e_1_3_2_99_2","doi-asserted-by":"publisher","DOI":"10.1021\/j100076a029"},{"key":"e_1_3_2_100_2","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b10026"},{"key":"e_1_3_2_101_2","doi-asserted-by":"publisher","DOI":"10.1021\/jp100402x"},{"key":"e_1_3_2_102_2","doi-asserted-by":"publisher","DOI":"10.1071\/CH9741617"}],"container-title":["Science"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/syndication.highwire.org\/content\/doi\/10.1126\/science.abg5526","content-type":"unspecified","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/www.science.org\/doi\/pdf\/10.1126\/science.abg5526","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2024,1,15]],"date-time":"2024-01-15T17:59:31Z","timestamp":1705341571000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.science.org\/doi\/10.1126\/science.abg5526"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,4,9]]},"references-count":101,"journal-issue":{"issue":"6538","published-print":{"date-parts":[[2021,4,9]]}},"alternative-id":["10.1126\/science.abg5526"],"URL":"https:\/\/doi.org\/10.1126\/science.abg5526","relation":{},"ISSN":["0036-8075","1095-9203"],"issn-type":[{"value":"0036-8075","type":"print"},{"value":"1095-9203","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,4,9]]}}}