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dc.contributor.authorReeves, Emily K.
dc.contributor.authorHumke, Jenna N.
dc.contributor.authorNeufeldt, Sharon R.
dc.date.accessioned2019-10-23T16:19:26Z
dc.date.available2019-10-23T16:19:26Z
dc.date.issued2019-09
dc.identifier.citationReeves, Emily K., Jenna N. Humke, and Sharon R. Neufeldt. “N-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki–Miyaura Cross Coupling.” The Journal of Organic Chemistry 84, no. 18 (September 2, 2019): 11799–11812. doi:10.1021/acs.joc.9b01692.en_US
dc.identifier.issn0022-3263
dc.identifier.urihttps://scholarworks.montana.edu/xmlui/handle/1/15723
dc.description.abstractTwo N-heterocyclic carbene ligands provide orthogonal chemoselectivity during the Pd-catalyzed Suzuki–Miyaura (SM) cross-coupling of chloroaryl triflates. The use of SIPr [SIPr = 1,3-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene] leads to selective cross-coupling at chloride, while the use of SIMes [SIMes = 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene] provides selective coupling at triflate. With most chloroaryl triflates and arylboronic acids, ligand-controlled selectivity is high (≥10:1). The scope of this methodology is significantly more general than previously reported methods for selective SM coupling of chloroaryl triflates using phosphine ligands. Density functional theory studies suggest that palladium’s ligation state during oxidative addition is different with SIMes compared to SIPr.en_US
dc.description.sponsorshipDivision of Chemistry (146121813379081848090); Division of Biological Infrastructure (1532078); M.J. Murdock Charitable Trust (2015066:MNL); Division of Advanced Cyberinfrastructure (1548562); National Institute of General Medical Sciences (P20GM103546); Montana State Universityen_US
dc.rightsThis Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s).en_US
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en_US
dc.titleN-Heterocyclic Carbene Ligand-Controlled Chemodivergent Suzuki–Miyaura Cross Couplingen_US
dc.typeArticleen_US
mus.citation.extentfirstpage11799en_US
mus.citation.extentlastpage11812en_US
mus.citation.issue18en_US
mus.citation.journaltitleJournal of Organic Chemistryen_US
mus.citation.volume84en_US
mus.identifier.doi10.1021/acs.joc.9b01692en_US
mus.relation.collegeCollege of Letters & Scienceen_US
mus.relation.departmentChemistry & Biochemistry.en_US
mus.relation.universityMontana State University - Bozemanen_US
mus.data.thumbpage6en_US


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