Introducing N-Heterocyclic Iminophosphoranes (NHIPs): Synthesis by [3 + 2] Cycloaddition of Azophosphines with Alkynes and Reactivity Studies was written by Tanaka, Keita;Riu, Martin-Louis Y.;Valladares, Brian;Cummins, Christopher C.. And the article was included in Inorganic Chemistry in 2022.SDS of cas: 700-16-3 The following contents are mentioned in the article:
Azophosphines (Ar-N:N-PR2) were prepared from N-aryl-N’-(trimethylsilyl)diazenes (Ar-N:N-SiMe3) and R2PCl by Me3SiCl elimination or oxidation of phosphinohydrazines (Ar-NH-NH-PR2) by 2,5-dialkyl-1,4-benzoquinones. Azophosphines underwent 1,3-dipolar cycloaddition with cyclooctyne and dimethylacetylene dicarboxylate to give N-heterocyclic iminophosphoranes (NHIPs), which are structurally similar to cyclic (alkyl)(amino)carbenes. The cycloaddition reaction is compatible with various P atom substituents including Ph (NHIP-1,4,6), iso-Pr (NHIP-2), cyclohexyl (NHIP-3), and dimethylamino (NHIP-5) groups. The pKBH+ values of the NHIPs in MeCN range from 13.13 to 23.14. From the Huynh electronic parameter, NHIP-1 and NHIP-2 have σ-donor strengths comparable with that of 1,8-diazabicyclo[5.4.0]undec-7-ene. NHIP-1 underwent facile 1,2-addition with pentafluoropyridine to form a rare fluorophosphorane. The treatment of NHIP-1 with triphenylsilane resulted in P-N bond cleavage, accompanied by the reduction of P(V) to P(III). A homoleptic, cationic Cu(I)-NHIP-1 complex was also prepared The potential utility of π-donating NHIPs was demonstrated by the stabilization of a reactive iminoborane (Cl-BN-SiMe3). The facile scalable synthesis, tunability of steric demands, and basicity of NHIPs suggest that this new heterocycle class may find a wide range of applications in synthetic chem. This study involved multiple reactions and reactants, such as 2,3,4,5,6-Perfluoropyridine (cas: 700-16-3SDS of cas: 700-16-3).
2,3,4,5,6-Perfluoropyridine (cas: 700-16-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.SDS of cas: 700-16-3