Bettinger, Holger F. published the artcileMetal-free conversion of methane and cycloalkanes to amines and amides by employing a borylnitrene, Synthetic Route of 25240-59-9, the publication is Angewandte Chemie, International Edition (2008), 47(25), 4744-4747, database is CAplus and MEDLINE.
C-H insertion: Borylnitrenes, which were generated in situ by photolysis of azides, convert unactivated alkanes by intermol. C-H insertion into aminoboranes, which in turn can be reacted further to give amines or amides. The boryl group serves two purposes: it converts the nitrene into a highly reactive BN vinylidene analog, and it is easily cleaved from the product. Caution: B azides may be explosive, and appropriate precautions must be taken when handling these compounds To study the reaction of catechol borylnitrene (C6H4O2BN:, 1a) with methane, the authors isolated 2-azido-1,3,2-benzodioxaborole (C6H4O2BN3, 3a) in Ar doped with methane (1-2% CH4 or CD4) at 10 K. Photolysis of 3a using UV irradiation resulted in the complete disappearance of 3a, the concomitant formation of nitrene C6H4O2BN: (1a) and of aminoborane C6H4O2BN(H)Me (2a) according to IR spectra and DFT calculations of vibrational modes. Reaction of trimethylsilyl azide and 2-chloro-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (pinacolboron chloride (pinBCl)) gave 2-azido-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3b, pinacolboron azide (pinBN3)) in 96% yield. Photolysis of 3b in cycloalkane solutions at room temperature afforded the expected aminoboranes pinBN(H)R (R = cyclopentyl, cyclohexyl, cycloheptyl) in 79% to 85% yield. The aminoboranes can conveniently be transformed into the corresponding primary amines or amides by alcoholysis or acylation, resp. The mol. structures of pinBN(H)R (R = cyclopentyl, cyclohexyl) were determined by x-ray crystallog.
Angewandte Chemie, International Edition published new progress about 25240-59-9. 25240-59-9 belongs to alcohols-buliding-blocks, auxiliary class Boronic acid and ester,Boronic Acids,Boronate Esters, name is 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-ol, and the molecular formula is C6H13BO3, Synthetic Route of 25240-59-9.
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