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Your search keyword '"Dale J. Wilger"' showing total 3 results
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3 results on '"Dale J. Wilger"'

1. Nickel-Catalyzed Hydroarylation of Alkynes under Reductive Conditions with Aryl Bromides and Water

Author

E Ryan Barber, Holli E Lemons, Hannah M Hynds, Dale J. Wilger, Emily T Fredrickson, and Claudia P Stephens

Subjects
chemistry.chemical_element, 010402 general chemistry, Hydrocarbons, Aromatic, 01 natural sciences, Coupling reaction, Catalysis, chemistry.chemical_compound, Coordination Complexes, Nickel, Molecular Structure, 010405 organic chemistry, Extramural, Aryl, Organic Chemistry, Water, Substrate (chemistry), Stereoisomerism, Combinatorial chemistry, Hydrocarbons, Brominated, 0104 chemical sciences, chemistry, Deuterium, Alkynes, Selectivity, Oxidation-Reduction
Abstract

An operationally simple nickel-catalyzed hydroarylation reaction for alkynes is described. This three-component coupling reaction utilizes commercially available alkynes and aryl bromides, along with water and Zn. An air-stable and easily synthesized Ni(II) precatalyst is the only entity used in the reaction that is not commercially available. This reductive cross-coupling reaction displays a fairly unusual anti selectivity when aryl bromides with ortho substituents are used. In addition to optimization data and a preliminary substrate scope, complementary experiments including deuterium labeling studies are used to provide a tentative catalytic mechanism. We believe this report should inspire and inform other Ni-catalyzed carbofunctionalization reactions.

Published
2019
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2. ChemInform Abstract: Catalytic Hydrotrifluoromethylation of Styrenes and Unactivated Aliphatic Alkenes via an Organic Photoredox System

Author

David A. Nicewicz, Dale J. Wilger, and Nathan J. Gesmundo

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, chemistry, Reagent, Thiophenol, Substrate (chemistry), Sodium trifluoromethanesulfinate, Salt (chemistry), Organic chemistry, Regioselectivity, General Medicine, Stoichiometry, Catalysis
Abstract

Herein is presented a direct method for the metal-free hydrotrifluoromethylation of alkenes. The method relies on the single electron oxidation of a commercially available sodium trifluoromethanesulfinate salt (CF3SO2Na, Langlois reagent) by N-Me-9-mesityl acridinium as a photoredox catalyst. Methyl thiosalicylate is used as a substoichiometric H-atom donor for aliphatic alkenes, and thiophenol is used as a stoichiometric H-atom donor for styrenyl substrates. The substrate scope for the transformation is broad, including mono-, di- and trisubstituted aliphatic and styrenyl alkenes, with high regioselectivity in nearly all cases examined.

Published
2013
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3. Catalytic hydrotrifluoromethylation of styrenes and unactivated aliphatic alkenes via an organic photoredox system

Author

Nathan J. Gesmundo, David A. Nicewicz, and Dale J. Wilger

Subjects
chemistry.chemical_classification, chemistry.chemical_compound, chemistry, Thiophenol, Reagent, Sodium trifluoromethanesulfinate, Organic chemistry, Substrate (chemistry), Regioselectivity, Salt (chemistry), General Chemistry, Stoichiometry, Catalysis
Abstract

Herein is presented a direct method for the metal-free hydrotrifluoromethylation of alkenes. The method relies on the single electron oxidation of a commercially available sodium trifluoromethanesulfinate salt (CF3SO2Na, Langlois reagent) by N-Me-9-mesityl acridinium as a photoredox catalyst. Methyl thiosalicylate is used as a substoichiometric H-atom donor for aliphatic alkenes, and thiophenol is used as a stoichiometric H-atom donor for styrenyl substrates. The substrate scope for the transformation is broad, including mono-, di- and trisubstituted aliphatic and styrenyl alkenes, with high regioselectivity in nearly all cases examined.

Published
2013
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