More Like this

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)

   null (Ed.)
2. 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. 

   more » « less
3. 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. 

   more » « less
4. C–F Bonds as “Frozen” Nucleophiles: Unconsummated S _N 2 Reactions

   https://doi.org/10.1021/acs.joc.2c01788  

   Harry, Stefan Andrew; Garrison, Nathaniel G.; Zhu, Andrea; Xiang, Michael Richard; Siegler, Maxime A.; Lectka, Thomas (October 2022, The Journal of Organic Chemistry)
5. Suzuki–Miyaura cross-coupling of amides and esters at room temperature: correlation with barriers to rotation around C–N and C–O bonds

   Lei, Peng; Meng, Guangrong; Shi, Shicheng; Ling, Yun; An, Jie; Szostak, Roman; Szostak, Michal (August 2017, Chemical science)

   The Suzuki-Miyaura cross-coupling has been widely recognized as one of the most important methods for the construction of C–C bonds. However, in contrast to traditional aryl halide or pseudohalide electrophiles, coupling reactions with unactivated C–N and C–O electrophiles have proven significantly more challenging. Here we report the first general palladium-catalyzed Suzuki-Miyaura cross-coupling of both common amides and aryl esters through the selective cleavage of the C–N and C–O bonds under exceedingly mild conditions. Notably, for the first time we demonstrate selective C(acyl)– N and C(acyl)–O cleavage/cross-coupling under the same reaction conditions. The reaction uses a commercially available, bench-stable and operationally-convenient (n3-1-t-Bu-indenyl)Pd(IPr)(Cl) precatalyst. Furthermore, we demonstrate that the reactivity of generic amides and aryl esters can be correlated with barriers to isomerization around the C(acyl)–X (X = N, O) bond, thus providing a blueprint for the development of a broad range of novel coupling reactions of ester and amide electrophiles by the selective activation of C–O and C–N bonds. 

   more » « less