TY - JOUR
T1 - Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates
AU - Himo, Fahmi
AU - Lovell, Timothy
AU - Hilgraf, Robert
AU - Rostovtsev, Vsevolod V.
AU - Noodleman, Louis
AU - Sharpless, K. Barry
AU - Fokin, Valery V.
PY - 2005/1/12
Y1 - 2005/1/12
N2 - Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles.
AB - Huisgen's 1,3-dipolar cycloadditions become nonconcerted when copper(I) acetylides react with azides and nitrile oxides, providing ready access to 1,4-disubstituted 1,2,3-triazoles and 3,4-disubstituted isoxazoles, respectively. The process is highly reliable and exhibits an unusually wide scope with respect to both components. Computational studies revealed a stepwise mechanism involving unprecedented metallacycle intermediates, which appear to be common for a variety of dipoles.
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U2 - 10.1021/ja0471525
DO - 10.1021/ja0471525
M3 - Article
C2 - 15631470
AN - SCOPUS:11844255741
VL - 127
SP - 210
EP - 216
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 1
ER -