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1. α-Amino Radical-Mediated Diverse Difunctionalization of Alkenes: Construction of C–C, C–N, and C–S Bonds

   https://doi.org/10.1021/acscatal.0c04243  

   Su, Yong-Liang; Tram, Linh; Wherritt, Daniel; Arman, Hadi; Griffith, Wendell P.; Doyle, Michael P. (November 2020, ACS Catalysis)

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2. Accessing sulfonamides via formal SO2 insertion into C–N bonds

   https://doi.org/10.1038/s41557-025-01848-2  

   Kim, Myojeong; Obertone, Carys E; Kelly, Christopher B; Reiher, Christopher A; Grosanu, Cristina; Robertson, James C; Levin, Mark D (August 2025, Nature Chemistry)
3. Cooperativity between H-bonds and tetrel bonds. Transformation of a noncovalent C⋯N tetrel bond to a covalent bond

   https://doi.org/10.1039/D3CP04430K  

   Wang, Xin; Li, Qingzhong; Scheiner, Steve (November 2023, Physical Chemistry Chemical Physics)

   Both a long noncovalent C⋯N tetrel bond and a short covalent C–N bond between imidazole and F₂CO represent minima of comparable energy, when the cooperativity of a H-bond is introduced into the system. 

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4. Conformational control through co-operative nonconventional C—H...N hydrogen bonds

   https://doi.org/10.1107/S2053229621007427  

   Bosch, Eric; Bowling, Nathan P.; Oburn, Shalisa M. (August 2021, Acta Crystallographica Section C Structural Chemistry)

   null (Ed.)

   We report the design, synthesis, and crystal structure of a conjugated aryleneethynyl molecule, 2-(2-{4,5-dimethoxy-2-[2-(2,3,4-trifluorophenyl)ethynyl]phenyl}ethynyl)-6-[2-(pyridin-2-yl)ethynyl]pyridine, C 30 H 17 F 3 N 2 O 2 , that adopts a planar rhombus conformation in the solid state. The molecule crystallizes in the space group P -1, with Z = 2, and features two intramolecular sp 2 -C—H...N hydrogen bonds that co-operatively hold the arylethynyl molecule in a rhombus conformation. The H atoms are activated towards hydrogen bonding since they are situated on a trifluorophenyl ring and the H...N distances are 2.470 (16) and 2.646 (16) Å, with C—H...N angles of 161.7 (2) and 164.7 (2)°, respectively. Molecular electrostatic potential calculations support the formation of C—H...N hydrogen bonds to the trifluorophenyl moiety. Hirshfeld surface analysis identifies a self-complementary C—H...O dimeric interaction between adjacent 1,2-dimethoxybenzene segments that is shown to be common in structures containing that moiety. 

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5. Synthon Substitution via C–I···π and C–I···N Halogen Bonds in Cocrystals of Anthracene-Based Organic Semiconductor Isosteres

   https://doi.org/10.1021/acs.cgd.5c01513  

   Bondarenko, Ivan; Ahuja, Shivani; Patrick, Brian O; Campillo-Alvarado, Gonzalo (January 2026, Crystal Growth & Design)

   Cocrystallization is a versatile supramolecular synthetic strategy for tuning the properties of organic semiconductors (OSCs) and related polycyclic aromatic hydrocarbons (PAHs) by controlling their packing and architectures with suitable coformers. In this study, we demonstrate a supramolecular synthon substitution approach to afford cocrystals of 9,10-diphenylanthracene (DPA) and its isostere 9,10-dipyridylanthracene (DPyA) with halogenated coformers 1,2-diiodotetrafluorobenzene (1,2-C6I2F4), 1,4-diiodotetrafluorobenzene (1,4-C6I2F4), and 1,3,5-triiodotrifluorobenzene (1,3,5-C6I3F3). The strategy enables reliable replacement of [C–I···π] interactions in DPA cocrystals with [C–I···N] interactions in the corresponding DPyA cocrystals. Although coformers and substitutions alter the supramolecular architectures, the photophysical properties and molecular conformations of the OSC building blocks remain largely preserved. The results highlight synthon substitution as a reliable supramolecular design element that accelerates the derivatization of established OSCs and their isosteres, offering opportunities for property modulation. 

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