{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,15]],"date-time":"2026-10-15T20:41:45Z","timestamp":1792096905264,"version":"4.4.0"},"reference-count":40,"publisher":"American Chemical Society (ACS)","issue":"11","license":[{"start":{"date-parts":[[2022,3,8]],"date-time":"2022-03-08T00:00:00Z","timestamp":1646697600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2022,3,8]],"date-time":"2022-03-08T00:00:00Z","timestamp":1646697600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2022,3,8]],"date-time":"2022-03-08T00:00:00Z","timestamp":1646697600000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100006606","name":"Natural Science Foundation of Tianjin City","doi-asserted-by":"publisher","award":["20JCJQJC00030"],"award-info":[{"award-number":["20JCJQJC00030"]}],"id":[{"id":"10.13039\/501100006606","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006606","name":"Natural Science Foundation of Tianjin City","doi-asserted-by":"publisher","award":["20JCZDJC00720"],"award-info":[{"award-number":["20JCZDJC00720"]}],"id":[{"id":"10.13039\/501100006606","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100004945","name":"Nankai University","doi-asserted-by":"publisher","award":["63181206"],"award-info":[{"award-number":["63181206"]}],"id":[{"id":"10.13039\/501100004945","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002855","name":"Ministry of Science and Technology of the People's Republic of China","doi-asserted-by":"publisher","award":["2021YFA1500200"],"award-info":[{"award-number":["2021YFA1500200"]}],"id":[{"id":"10.13039\/501100002855","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100018594","name":"Central University Basic Research Fund of China","doi-asserted-by":"publisher","award":["2122018165"],"award-info":[{"award-number":["2122018165"]}],"id":[{"id":"10.13039\/501100018594","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["21871147"],"award-info":[{"award-number":["21871147"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["91956106"],"award-info":[{"award-number":["91956106"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Haihe Laboratory of Sustainable Chemical Transformations"},{"name":"Tencent Foundation"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Am. Chem. Soc."],"published-print":{"date-parts":[[2022,3,23]]},"DOI":"10.1021\/jacs.2c00962","type":"journal-article","created":{"date-parts":[[2022,3,8]],"date-time":"2022-03-08T11:46:19Z","timestamp":1646739979000},"page":"4810-4818","source":"Crossref","is-referenced-by-count":133,"title":["Borane-Catalyzed C3-Alkylation of Pyridines with Imines, Aldehydes, or Ketones as Electrophiles"],"prefix":"10.1021","volume":"144","author":[{"given":"Zhong","family":"Liu","sequence":"first","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jia-Hao","family":"He","sequence":"additional","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ming","family":"Zhang","sequence":"additional","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhu-Jun","family":"Shi","sequence":"additional","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Han","family":"Tang","sequence":"additional","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xin-Yue","family":"Zhou","sequence":"additional","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jun-Jie","family":"Tian","sequence":"additional","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5863-0804","authenticated-orcid":true,"given":"Xiao-Chen","family":"Wang","sequence":"additional","affiliation":[{"name":"State Key Laboratory and Institute of Elemento-Organic Chemistry, Haihe Laboratory of Sustainable Chemical Transformations, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2022,3,8]]},"reference":[{"key":"ref1\/cit1","doi-asserted-by":"publisher","DOI":"10.1021\/jm501100b"},{"key":"ref2\/cit2","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrev.7b00021"},{"key":"ref3\/cit3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201611724"},{"key":"ref4\/cit4","doi-asserted-by":"publisher","DOI":"10.1021\/ja401146v"},{"key":"ref5\/cit5","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.1c03257"},{"key":"ref6\/cit6","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)97768-3"},{"key":"ref7\/cit7","doi-asserted-by":"publisher","DOI":"10.1038\/nature11680"},{"key":"ref8\/cit8","doi-asserted-by":"publisher","DOI":"10.1021\/ja406223k"},{"key":"ref9\/cit9","doi-asserted-by":"publisher","DOI":"10.1038\/nature14885"},{"key":"ref10\/cit10","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-021-03637-6"},{"key":"ref11\/cit11","doi-asserted-by":"publisher","DOI":"10.1126\/science.aas8961"},{"key":"ref12\/cit12","doi-asserted-by":"publisher","DOI":"10.1038\/s41586-021-03567-3"},{"key":"ref13\/cit13","doi-asserted-by":"publisher","DOI":"10.1021\/ja209510q"},{"key":"ref14\/cit14","doi-asserted-by":"publisher","DOI":"10.1021\/ja2021075"},{"key":"ref15\/cit15","doi-asserted-by":"publisher","DOI":"10.1021\/om400890p"},{"key":"ref16\/cit16","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200503047"},{"key":"ref17\/cit17","doi-asserted-by":"publisher","DOI":"10.1021\/ja076498n"},{"key":"ref18\/cit18","doi-asserted-by":"publisher","DOI":"10.1021\/ja412563e"},{"key":"ref19\/cit19","doi-asserted-by":"publisher","DOI":"10.1021\/ja511352u"},{"key":"ref20\/cit20","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.9b03138"},{"key":"ref21\/cit21","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-021-00792-1"},{"key":"ref22\/cit22","doi-asserted-by":"publisher","DOI":"10.1039\/C0SC00419G"},{"key":"ref23\/cit23","doi-asserted-by":"publisher","DOI":"10.1126\/science.1134230"},{"key":"ref24\/cit24","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf7229"},{"key":"ref25\/cit25","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b03147"},{"key":"ref26\/cit26","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.5b09209"},{"key":"ref27\/cit27","doi-asserted-by":"publisher","DOI":"10.1002\/ange.201702304"},{"key":"ref28\/cit28","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202007352"},{"key":"ref29\/cit29","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.1c02876"},{"key":"ref30\/cit30","doi-asserted-by":"publisher","DOI":"10.1246\/cl.1984.1255"},{"key":"ref31\/cit31","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201508181"},{"key":"ref32\/cit32","doi-asserted-by":"publisher","DOI":"10.1038\/s41557-018-0178-5"},{"key":"ref33\/cit33","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202016771"},{"key":"ref34\/cit34","unstructured":"The hydroboration (or\nhydrosilylation) reaction of pyridine\n                      1a\n                      gave identical\nor very similar yields in THF and THF-\n                      d\n                      8\n                      if stringent Schlenk techniques were applied during the workup.\nBecause Bpin (or silyl)\u2013protected 1,4-DHPs could be easily\nhydrolyzed or oxidized, reactions performed in THF-\n                      d\n                      8\n                      were used for determination of the NMR yields of 1,4-DHPs\n(shown in Table 1)\nfor convenience and better reproducibility."},{"key":"ref35\/cit35","unstructured":"The reaction of unsubstituted\npyridine with the use of 1.5 equiv of imine\n                      2a\n                      gave monoalkylation\nproduct\n                      3bb-mono\n                      in 12% yield and dialkylation product\n                      3bb\n                      in 26% yield; whereas the reaction of 2-phenylpyridine\nwith the use of 2 equiv of imine\n                      2a\n                      gave monoalkylation\nproduct\n                      3cc-mono\n                      in 10% yield and dialkylation product\n                      3cc-di\n                      in 20% yield."},{"key":"ref36\/cit36","doi-asserted-by":"publisher","DOI":"10.1021\/acscatal.8b01166"},{"key":"ref37\/cit37","unstructured":"The\nreaction of pyridine\n                      1a\n                      with a ketone also generated\nthe ketone reduction byproduct,\nso the ketone might act as a sacrificial hydride acceptor as well.\nFor details, see the Supporting Information. Because the reactions\nwith aldehydes gave dehydroxylated products, dehydroxylation should\nhave consumed the released hydride from oxidative aromatization."},{"key":"ref38\/cit38","unstructured":"For calculation results\nof the unfavorable pathways, see Fig. S1 and Fig. S2 in the Supporting\nInformation. The pathways for monoalkylation and dialkylation with\nunsubstituted pyridine were evaluated computationally; the results\nindicated that dialkylation was more energetically favorable. For\ndetails, see Fig. S3 in the Supporting Information."},{"key":"ref39\/cit39","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200903005"},{"key":"ref40\/cit40","doi-asserted-by":"publisher","DOI":"10.1039\/C9RA01468C"}],"container-title":["Journal of the American Chemical Society"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/jacs.2c00962","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,4,26]],"date-time":"2023-04-26T20:16:25Z","timestamp":1682540185000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/doi\/10.1021\/jacs.2c00962"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,3,8]]},"references-count":40,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2022,3,23]]}},"alternative-id":["10.1021\/jacs.2c00962"],"URL":"https:\/\/doi.org\/10.1021\/jacs.2c00962","relation":{},"ISSN":["0002-7863","1520-5126"],"issn-type":[{"value":"0002-7863","type":"print"},{"value":"1520-5126","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,3,8]]}}}