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dc.contributor.authorRussell, John E.
dc.contributor.authorEntz, Emily D.
dc.contributor.authorJoyce, Ian M.
dc.contributor.authorNeufeldt, Sharon R.
dc.date.accessioned2019-06-07T19:53:33Z
dc.date.available2019-06-07T19:53:33Z
dc.date.issued2019-04
dc.identifier.citationRussell, John E. A., Emily D. Entz, Ian M. Joyce, and Sharon R. Neufeldt. "Nickel-Catalyzed Stille Cross Coupling of C-O Electrophiles." ACS Catalysis 9, no. 4 (April 2019): 3304-3310. DOI:10.1021/acscatal.9b00744.en_US
dc.identifier.issn2155-5435
dc.identifier.urihttps://scholarworks.montana.edu/xmlui/handle/1/15494
dc.description.abstractAryl sulfamates, tosylates, and mesylates undergo efficient Ni-catalyzed cross coupling with diverse organostannanes in the presence of relatively unhindered alkylphosphine ligands and KF. The coupling is valuable for difficult bond constructions, such as aryl-heteroaryl, aryl-alkenyl, and aryl-alkynyl, using nontriflate phenol derivatives. A combination of experimental and computational studies implicates an unusual mechanism for transmetalation involving an 8-centered cyclic transition state. This reaction is inhibited by chloride sources due to slow transmetalation of organostannanes at a Ni(II)-chloride intermediate. These studies help to explain why prior efforts to achieve Ni-catalyzed Stille coupling of phenol derivatives were unsuccessful.en_US
dc.description.sponsorshipMontana State University; NSF grant no. ACI-1548562; NSF-MRI:DBI-1532078; Murdock Charitable Trust Foundation;en_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.titleNickel-Catalyzed Stille Cross Coupling of C-O Electrophilesen_US
dc.typeArticleen_US
mus.citation.extentfirstpage3304en_US
mus.citation.extentlastpage3310en_US
mus.citation.issue4en_US
mus.citation.journaltitleACS Catalysisen_US
mus.citation.volume9en_US
mus.identifier.categoryChemical & Material Sciencesen_US
mus.identifier.doi10.1021/acscatal.9b00744en_US
mus.relation.collegeCollege of Letters & Scienceen_US
mus.relation.departmentChemistry & Biochemistry.en_US
mus.relation.universityMontana State University - Bozemanen_US
mus.data.thumbpage4en_US


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