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Esters as Radical Acceptors: β‐NHC‐Borylalkenyl Radicals Induce Lactonization by C−C Bond Formation/Cleavage on Esters

https://doi.org/10.1002/anie.201902001

Shimoi, Masaki; Maeda, Katsuhiro; Geib, Steven J.; Curran, Dennis P.; Taniguchi, Tsuyoshi (April 2019, Angewandte Chemie International Edition)

Abstract Substituted propargyl acetates are converted into 4‐boryl‐2(5H)‐furanones upon thermolysis in the presence of an N‐heterocyclic carbene borane (NHC‐borane) and di‐tert‐butyl peroxide. The acetyl methyl group is lost during the reaction as methane. Evidence suggests that the reaction proceeds by a sequence of radical events including: 1) addition of an NHC‐boryl radical to the triple bond; 2) cyclization of the resultant β‐borylalkenyl radical to the ester carbonyl group; 3) β‐scission of the so‐formed alkoxy radical to provide the 4‐boryl‐2(5H)‐furanone and a methyl radical; and 4) hydrogen abstraction from the NHC‐borane to return the initial NHC‐boryl radical and methane.
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Facile Synthesis of α-N-Heterocyclic Carbene-Boryl Ketones from N-Heterocyclic Carbene-Boranes and Alkenyl Triflates

https://doi.org/10.1021/jacs.9b05547

Dai, Wen; Geib, Steven J.; Curran, Dennis P. (July 2019, Journal of the American Chemical Society)

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Ring-Opening Reactions of NHC-Boriranes with In Situ Generated HCl: Synthesis of a New Class of NHC-Boralactones

https://doi.org/10.1021/jacs.8b13010

Dai, Wen; Geib, Steven J.; Curran, Dennis P. (February 2019, Journal of the American Chemical Society)

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EPR and Preparative Studies of 5- endo Cyclizations of Radicals Derived from Alkenyl NHC-Boranes Bearing tert -Butyl Ester Substituents

https://doi.org/10.1021/acs.joc.8b03112

Dai, Wen; Curran, Dennis P.; Walton, John C. (January 2019, The Journal of Organic Chemistry)

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Synthesis and characterization of N-heterocyclic carbene complexes of 1,3,2-dioxaborolane-4,5-dione (NHC-boryl oxalates)

https://doi.org/10.1016/j.tet.2018.10.031

Bolt, Daniel A.; Geib, Steven J.; Curran, Dennis P. (December 2018, Tetrahedron)

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5- Endo Cyclizations of NHC-Boraallyl Radicals Bearing Ester Substituents: Characterization of Derived 1,2-Oxaborole Radicals and Boralactones

https://doi.org/10.1021/jacs.8b09288

Dai, Wen; McFadden, Timothy R.; Curran, Dennis P.; Früchtl, Herbert A.; Walton, John C. (November 2018, Journal of the American Chemical Society)

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Difluorination at Boron Leads to the First Electrophilic Ligated Boryl Radical (NHC-BF ₂ ^. )

https://doi.org/10.1002/anie.201806476

Subervie, Daniel; Graff, Bernadette; Nerkar, Swapnil; Curran, Dennis P.; Lalevée, Jacques; Lacôte, Emmanuel (August 2018, Angewandte Chemie International Edition)
Radical trans -Hydroboration of Alkynes with N-Heterocyclic Carbene Boranes

https://doi.org/10.1002/anie.201804515

Shimoi, Masaki; Watanabe, Takashi; Maeda, Katsuhiro; Curran, Dennis P.; Taniguchi, Tsuyoshi (July 2018, Angewandte Chemie International Edition)

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Reactions of N-Heterocyclic Carbene Boranes with 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione: Synthesis of Mono- and Bis-hydrazonyl NHC-Boranes

https://doi.org/10.1021/acs.joc.8b01125

Dai, Wen; Geib, Steven J.; Curran, Dennis P. (May 2018, The Journal of Organic Chemistry)

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Tris(trimethylsilyl)silane-mediated Reductive Decyanation and Cyano Transfer Reactions of Malononitriles

https://doi.org/10.1246/cl.171231

Kawamoto, Takuji; Shimaya, Yudai; Curran, Dennis P.; Kamimura, Akio (April 2018, Chemistry Letters)

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