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Detailed Mechanistic Study of Radical Mediated Chemoselective Phosphination of Aryl Halide
Author(s) -
Kosar Naveen,
Mahmood Tariq,
Hafeez Farhan,
Ayub Khurshid
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801495
Subject(s) - halide , aryl , iodide , chemistry , bromide , combinatorial chemistry , catalysis , supramolecular chemistry , catalytic cycle , computational chemistry , photochemistry , organic chemistry , molecule , alkyl
Phosphines play important role in organic synthesis, since they are important ligands for transition metals catalysis. Moreover, phosphines are important building blocks of supramolecular architectures, and are used in advanced material sciences. An important reaction to make phosphines is the phosphination of organic halides. In this report, the mechanistic details of radical initiated phosphination of organic halides are studied theoretically for complete reaction cycle. The mechanistic studies are performed with an accurate method (ωB97XD), which we established for similar reactions through a benchmark study. The mechanistic studies are performed with aryl bromide and aryl iodide. The results show that overall reaction follows S H 2 pathway, and all steps are thermodynamically and kinetically favorable. The mechanistic outcomes of the research are in nice agreement with the recent experimental observations.