Regio- and Stereoselective Synthesis of 1,1-Diborylalkenes via Bronsted Base-Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdan

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dc.contributor.authorLiu, Xiaocuien
dc.contributor.authorMing, Wenboen
dc.contributor.authorLuo, Xiaolingen
dc.contributor.authorFriedrich, Alexandraen
dc.contributor.authorMaier, Janen
dc.contributor.authorRadius, Udoen
dc.contributor.authorSantos, Webster L.en
dc.contributor.authorMarder, Todd B.en
dc.contributor.departmentChemistryen
dc.date.accessioned2021-01-05T14:13:20Zen
dc.date.available2021-01-05T14:13:20Zen
dc.date.issued2020-04en
dc.description.abstractThe NaOtBu-catalyzed mixed 1,1-diboration of terminal alkynes using the unsymmetrical diboron reagent BpinBdan (pin = pinacolato; dan = 1,8-diaminonaphthalene) proceeds in a regio- and stereoselective fashion affording moderate to high yields of 1,1-diborylalkenes bearing orthogonal boron protecting groups. It is applicable to gram-scale synthesis without loss of yield or selectivity. The mixed 1,1-diborylalkene products can be utilized in Suzuki-Miyaura cross-coupling reactions which take place selectivly at the C-B site. DFT calculations suggest the NaOtBu-catalyzed mixed 1,1-diboration of alkynes occurs through deprotonation of the terminal alkyne, stepwise addition of BpinBdan to the terminal carbon followed by protonation with tBuOH. Experimentally observed selective formation of (Z)-diborylalkenes is supported by our theoretical studies.en
dc.description.notesT. B. M. and U. R. thank the Julius-Maximilians-Universitat Wurzburg for support. W. L. S. thanks the NIH (Grant Number R01AI144026) for funding. X. Liu, W. Ming, and X. Luo are grateful to the China Scholarship Council for providing scholarships. We thank AllyChem Co. Ltd. for a generous gift of B<INF>2</INF>pin<INF>2</INF>.en
dc.description.sponsorshipJulius-Maximilians-Universitat Wurzburg; NIHUnited States Department of Health & Human ServicesNational Institutes of Health (NIH) - USA [R01AI144026]; China Scholarship CouncilChina Scholarship Councilen
dc.format.mimetypeapplication/pdfen
dc.identifier.doihttps://doi.org/10.1002/ejoc.202000128en
dc.identifier.eissn1099-0690en
dc.identifier.issn1434-193Xen
dc.identifier.issue13en
dc.identifier.pmid32362780en
dc.identifier.urihttp://hdl.handle.net/10919/101740en
dc.identifier.volume2020en
dc.language.isoenen
dc.rightsCreative Commons Attribution 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/en
dc.subjectBoronate estersen
dc.subjectBorylationen
dc.subjectCross-couplingen
dc.subjectSynthesis designen
dc.subjectStructure elucidationen
dc.titleRegio- and Stereoselective Synthesis of 1,1-Diborylalkenes via Bronsted Base-Catalyzed Mixed Diboration of Alkynyl Esters and Amides with BpinBdanen
dc.title.serialEuropean Journal of Organic Chemistryen
dc.typeArticle - Refereeden
dc.type.dcmitypeTexten
dc.type.dcmitypeStillImageen

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