An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine trans-tetrafluoro-λ⁶-sulfanyl triazoles

Abstract

An eccentric trans-SF4 unit achieves a rod-like linear connection of two independent N-heterocycles, pyridines and triazoles.

Studies of Halogen Bonding Induced by Pentafluorosulfanyl Aryl Iodides: A Potential Group of Halogen Bond Donors in a Rational Drug Design

“…More and more examples of biologically active SF 5 -containing drug candidates have been reported in recent years (Figure 1c) [35,38,39,40,41,42,43,44]. Extending our research to the design and synthesis of SF 5 -containing biologically attractive molecules [45,46,47,48,49,50,51,52,53,54,55,56,57] and a halogen bonding research program [58,59], we are interested in aryl iodides 1a – d consisting of SF 5 -group(s) in the benzene ring as potential drug fragments capable of halogen bonding, in particular, 3,5-bis-SF 5 -iodobenzene ( 1d , Figure 1d). In this research, we have examined the halogen bonding induced by SF 5 -aryl iodides 1a – d .…”

(Hetero)aryl‐SVI Fluorides: Synthetic Development and Opportunities

“…By means of single‐crystal XRD and DFT calculations, the authors disclosed an octahedral geometry with a trans configuration of the hypervalent S VI center. Furthermore, the trans ‐tetrafluoro‐λ 6 ‐sulfanes bearing an alkenyl group 115 were further derivatized through a thermal Huisgen 1,3‐dipolar cycloaddition to provide a wide range of three‐dimensional building blocks with two independent N‐heterocycles ( 117 , 118 ) [52] …”

“…Furthermore, the transtetrafluoro-λ 6 -sulfanes bearing an alkenyl group 115 were further derivatized through a thermal Huisgen 1,3-dipolar cycloaddition to provide a wide range of three-dimensional building blocks with two independent N-heterocycles (117, 118). [52] In 2020 Shibata and co-workers also reported the addition of Py-SF 4 Cl to terminal alkynes and alkenes under irradiation with light (1 W blue LED; Scheme 24C). This procedure is an excellent alternative to BEt 3 -catalyzed processes, as the borane is often the source of undesired side reactivity or substrate decomposition.…”

Studies of Halogen Bonding Induced by Pentafluorosulfanyl Aryl Iodides: A Potential Group of Halogen Bond Donors in a Rational Drug Design

“…[36][37][38][39][40][41] More and more examples of biologically active SF5-contaning drug candidates have been reported in recent years ( Figure 1c). [34,[37][38][39][40][41] Extending our research to the design and synthesis of SF5-containing biologically attractive molecules [42][43][44][45][46][47][48][49][50][51][52][53][54] and a halogen bonding research program, [55,56] we are interested in aryl iodides 1a-d consisting of SF5-group(s) in the benzene ring as potential drug fragments capable of halogen bonding, in particular, 3,5-bis-pentafluorosulfanyl iodobenzene 1d (Figure 1d).…”