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1. The Thermal Rearrangement of an NHC‐Ligated 3‐Benzoborepin to an NHC‐Boranorcaradiene

   https://doi.org/10.1002/ange.201912234  

   Shimoi, Masaki; Kevlishvili, Ilia; Watanabe, Takashi; Maeda, Katsuhiro; Geib, Steven J.; Curran, Dennis P.; Liu, Peng; Taniguchi, Tsuyoshi (November 2019, Angewandte Chemie)

   Abstract An N‐heterocyclic‐carbene‐ligated 3‐benzoborepin with a bridged structure has been synthesized by double radicaltrans‐hydroboration of benzo[3,4]cycloundec‐3‐ene‐1,5‐diyne with an N‐heterocyclic carbene borane. The thermal reaction of the NHC‐ligated borepin at 150 °C gives an isolable NHC‐boranorcaradiene. Experiments and density functional theory calculations support a mechanism whereby the borepin initially rearranges to a boranorcaradiene by a thermal 6π‐electrocyclic reaction. This is followed by 1,5‐boron shift to give a rearranged boranorcaradiene. This shift occurs with stereoinversion at boron through a transition state with open‐shell diradical character. This is the first example of the isolation of a boranorcaradiene from a thermal reaction of a borepin. 

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

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   Dai, Wen; Geib, Steven J.; Curran, Dennis P. (February 2019, Journal of the American Chemical Society)
4. [(NHC)PdCl ₂ (Aniline)] Complexes: Easily Synthesized, Highly Active Pd(II)–NHC Precatalysts for Cross-Coupling Reactions

   https://doi.org/10.1021/acs.joc.1c02183  

   Xia, Qinqin; Shi, Shicheng; Gao, Pengcheng; Lalancette, Roger; Szostak, Roman; Szostak, Michal (November 2021, The Journal of Organic Chemistry)
5. [(NHC)Pd(OAc) ₂ ]: Highly Active Carboxylate Pd(II)–NHC (NHC = N-Heterocyclic Carbene) Precatalysts for Suzuki–Miyaura and Buchwald–Hartwig Cross-Coupling of Amides by N–C(O) Activation

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   Zhu, Yawei; Yang, Shiyi; Zhou, Tongliang; Szostak, Michal (July 2024, The Journal of Organic Chemistry)