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Nishimura K., Xu S., Nishii Y., et al. One-Step Synthesis of Benzophosphole Derivatives from Arylalkynes by Phosphenium-Dication-Mediated Sequential C-P/C-C Bond Forming Reaction. Organic Letters. 25(9), 1503-1508, 10 March 2023; © 2023 American Chemical Society. https://doi.org/10.1021/acs.orglett.3c00263., A metal-free, phosphenium-dication-mediated sequential C-P and C-C bond forming reaction has been developed. This protocol can provide concise access to the (di)benzophosphole derivatives in one synthetic operation from the readily available and simple arylalkynes and phosphinic acids. Application to the multiple cyclization reaction and the fully intermolecular three-component-coupling-type reaction are also described.

This is the accepted version of the following article: Nakamura Shotaro, Okubo Kohei, Nishii Yuji, et al. Stimuli‐Responsive Properties on a Bisbenzofuropyrazine Core: Mechanochromism and Concentration‐Controlled Vapochromism. Chemistry – A European Journal, e202302605 (2023), which has been published in final form at https://doi.org/10.1002/chem.202302605. This article may be used for non-commercialpurposes in accordance with the Wiley Self-ArchivingPolicy [https://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html], Stimulus-responsive organic materials with luminescence switching properties have attracted considerable attention for their practical applications in sensing, security, and display devices. In this paper, bent-type bisbenzofuropyrazine derivatives, Bent-H and Bent-sBu, with good solubilities were synthesized, and their physical and optical properties were investigated in detail. Bent-H gave three crystalline polymorphs, and they showed different luminescence properties depending on their crystal packing structures. In addition, Bent-H exhibited mechanochromic luminescence in spite of its rigid skeleton. Bent-sBu exhibited unique concentration-dependent vapochromic luminescence. Ground Bent-sBu was converted to blue-emissive, green-emissive, and green-emissive high-viscosity solution states at low, moderate, and high concentrations of CHCl3 vapor, respectively. This finding represents a concentration-dependent multi-phase transition with an organic solvent, which is of potent interest for application in sensing systems.

The nitrogen atom is ubiquitous in bioactive molecules and functional materials, and the development of new CN bond forming strategies is thus one of the long-standing research subjects in the synthetic community. This account describes the nitrogen-umpolung-enabled copper-catalyzed highly chemo- and stereoselective amination protocols developed by the author’s research group. Starting from the CH amination, electrophilic amination of stable organoboron and organosilicon compounds, aminoboration/hydroamination of alkenes, and their applications to the synthesis of functionality-rich alkylamines are shown. The reaction design, concept, and substrate scope are briefly summarized.

A copper-mediated trifluoromethylthiolation of alkenyl iodides with AgSCF₃ has been developed. CuSCF₃ species generated in-situ from a copper salt and AgSCF₃ can be coupled with alkenyl iodides to produce the corresponding trifluoromethylthioalkenes efficiently. The reaction conditions are compatible with various functional groups. Moreover, its scale-up synthesis is also possible to provide the desired trifluoromethylthiolated product even on a gram-scale.