Science of Synthesis

Subramanian, L. R., Science of Synthesis, (2004) 19, 189.

Very good yields of aryl nitriles ‌61‌ are obtained by the palladium-catalyzed cyanation of aryl bromides ‌60‌ with zinc(II) cyanide under microwave irradiation.[‌28‌] Reaction times are shortened to a few minutes and reactions are carried out in dimethylformamide (‌Scheme 25‌). The experimental procedure is similar to that described for the preparation of unsaturated nitriles (Section ‌19.5.5.2‌). This method can be extended to the one-pot preparation of tetrazoles by tetrazole formation after microwave cyanation. Tetrazole formation is also conducted under microwave irradiation by treatment with sodium azide and ammonium chloride in dimethylformamide. This procedure is generally applicable in organic synthesis and, indeed, a potent C2-symmetric HIV-1 protease inhibitor containing several functional groups has been synthesized in this way from its dibromo precursor.[‌28‌]

‌Meeeee 88‌ Meeeeeeee-Meeeeeeee Meeeeeeeeeee ee Meee Meeeeeee eeee Meee(MM) Meeeeee eeeee Meeeeeeee Meeeeeeeeee[‌88‌]

Me eeeee eeeeee(MM) eeeeeee ee e eeeeeee ee eeeeee eeeeeee eee eeeeee(MM) eeeeeee ee eeeeeeeee eeeeeee, eee eee ee e eeeeeeeee eeeeeeee eee ee eeeeeee ee eee eeeeeeeee-eeeeeee eeeeeeeee ee eeee eeeeeeee ‌88‌ ee eeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌] Meee eeee eeeeeeeee ‌88‌ (M = Me), e eeeeeee ee eeeeee eeeeeee eee eeeeee(MM) eeeeeee ee eeee eeeeeee eee eeeeeeee eeeeeeee eee eee ee eeee eeeeeeeee ee eee eeeeeeeeeeeee eeee eeeeeeee (‌Meeeee 88‌). Mee eeeeeeee ee eeeeeee eee ee 8-eeeeeeeeeeeeeeee-8-eee eeee 8.8 eeeeeeeeeee ee eeeeee eeeeeee eee e eeeee eeeeee ee eeee, eeeeee eeee eeeeeee eeeeee. Meee eeee eeeeeee eeeeeeeee eeeeee eeeeeeeee eeeeeeeee eeeeeeee eee eeeee (e.e., 8-eeeee-8-eeeeeeeeeeee) ee eeeeeeeee eeeeeeeeeeeee (e.e., 8-eeeeeeeeeeeeeeeeee).

‌Meeeee 88‌ Meeeeeeee ee Meee Meeeeee eeee Meeeee(MM) Meeeeee ee Meeeee Meeeeee/Meeeee(MM) Meeeeee eeeee Meeeeeeee Meeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meee Meeeeeee ‌88‌ eeee Meee Meeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meee eeeeeeee eee eeeeeeeee-eeeeee eeeeeeeee ee eeeeee eeeeeee, eeeee eeeee eeeeeeeee eee eeeee ee. Meeeeeeee, ee ee eeeeeeeeee eeee ee eeeeeeeeeee eeeeee ee eeee ee e eeeeeeee-eeeeeeeee eeeeee.

MMMMMMM: Meeeeee eeeee eee ee eeeeeeee eeeeeee eee eeee eee eee eeeeeeeee eeeee.

M eee eeeee-eeeeee Meeee eeee eee eeeeeee eeee eeee eeeeeee ‌88‌ (8.8 eeee), Me(MM)8 (88.8 ee, 8.8 eeee), eee Me(MMe8)8 (8.8 ee, 8.8 μeee) ee MMM (8 eM). Mee eeeeeee eee eeeeee eeee M8 eee eee eeeee eee eeeeeeeee eeeeeeeeee eeeeee eeeeee eeee e Meeeeeeeeee. Mee eeeeeee eee eeeeeee ee eeeeeeeee eeeeeeeeeee (88 M) eee 8 eee. Mee eeeeeeee eeee eee eeeeeee ee eeeee ee eeeeee eee eeeeeee eee eeeeeee eeee MeMMe (88 eM) eee eeeeee eeee M8M. Mee eeeeeee eeeee eee eeeee, eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeee eeeeeeeeeeeeee ee eeee eee eeee eeeeeee.

References