Categories: C-N Bond Formation > Synthesis of azides >
Synthesis of allyl azides
Recent Literature
A direct catalytic azidation of primary, secondary, and tertiary allylic
alcohols affords the corresponding allylic azides in high to excellent yields
and regioselectivities. The reaction provides straightforward access to allylic
azides that are valuable intermediates in organic synthesis.
M. Rueping, C. Vila, U. Uria, Org. Lett., 2012,
14, 768-771.
A catalytic amount of iron trichloride enables C-C and C-N bond formation
reactions of O-heterocycles accompanied by ring opening in the presence
of TMSN3 or allylsilanes. The reactions smoothly proceeded at room
temperature to give the corresponding primary saturated alcohols from
2-substituted tetrahydrofurans, ortho-substituted benzyl alcohols from
phthalanes, and saturated carboxylic acids from lactones in high yields.
Y. Sawama, K. Shibata, Y. Sawama, M. Takubo, Y. Monguchi, N. Krause, H. Sajiki, Org. Lett., 2013,
15, 5282-5285.
A convenient and mild iron-catalyzed 1,2-azidoamidation of 1,3-dienes shows
excellent functional group compatibility to furnish versatile precursors to
1,2-diamine products with high levels of site, regio-, and stereoselectivity.
The reaction is proposed to proceed via a single electron transfer/radical
addition/C-N bond formation relay process.
Z.-Y. Dai, I. A. Guzei, J. M. Schomaker, Org. Lett., 2024,
26, 269-273.