Science of Synthesis

Subramanian, L. R., Science of Synthesis, (2004) 19, 191.

The Rosenmund–von Braun and transition-metal-catalyzed reactions applied to the preparation of aryl nitriles from aryl halides are also valid for the preparation of hetaryl nitriles from hetaryl halides. In many instances, examples of reactions with aryl and hetaryl halides are described and so a separate discussion of the two is not necessary. However, sometimes impediments creating problems with the methods when applied to hetaryl halides creep in and so these reactions must be discussed separately.

Mee eeee-eeeee eeeeeeeeeeeeee ‌88‌, ‌88‌, eee ‌88‌ eeeeeee eeeeee eeeeeeeeeeeeee eeee eee eeeeeeeeeeeee eeeeeeee ‌88‌, ‌88‌, eee ‌88‌ ee eeeeeee eeee eeeeee(M) eeeeeee ee eeeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee–eee Meeee Meeeeeee ee Meee-Meeee Meeeeeeeeeeeee eeee Meeeee(M) Meeeeee[‌88‌]

Mee eeeeee eeeeeeee-eeeeeeee eeeeee ee eee eeeee eeeee eeeeee eee eeeeeeee eeee ee 8-eeeeeeeeeeee-8-eeeee (‌88‌) eeeeeeeeee eeeeeeeeeeee eeeeee ee eee eeeeeee eee ee eee eeeeee eeee eeeeee ee eee eeeeeee. Meeee eeeeeee eeeeee eeee eeeeeeeee eeeeeee, eeeeeeeee-eeeeeeeee eeeeeeeee eeee eeeeeeeee eeeeee ee eee eeeeeeee ee 88-eeeee-8 eee eeeeee(M) eeeeee eeeeee eeeeeeeeee eee eeeeeeeeee eeee 8-eeeeeeeeeeeee-8-eeeeeeeeeeee (‌88‌) (‌Meeeee 88‌).[‌88‌,‌88‌] Me eee eeee eeeeee 8-eeeeeeeeeeeee-8,8-eeeeeeeeeeeeee ee eeee eeeeeeee ee 88% eeeee.[‌88‌]

‌Meeeee 88‌ Meeeeeeee-Meeeeeeee Meeeeeeeeeee ee e Meeeeeeeeeeee eeee Meeeeeeee Meeeeee ee eee Meeeeeee ee 88-Meeee-8 eee Meeeee(M) Meeeee[‌88‌]

8-Meeeeeeeeee 8-eeeeeeeeeeeee-8-eeeeeeeeeeeee ‌88‌ eeee eeee eeeeeeee ee eeee eeeeee ee eeeeeeee eee eeeeeeeeeeeee 8-eeeeeeeeeeee-8-eeeeee eeee eeeeee eeeeeeeeeeeeee, eeeeeeeee ee eeee eeee eeeeee eeeeeee eee eeeeee(M) eeeeeee, ee eeeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeeeee Meeee Meeeee Meeeeeeeeeeeee[‌88‌]

Meeeeee eeeeeeeee eeeeeee eeee eeeeeee eeeeeeeeeeee eeee eeee eeeeeeee ee eeee(MM) eeeeeee ee eee eeeeeeee ee eeee eeeeee eee e eeeeeeeee eeeeeeee ee eeeeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeee (e.e., ‌Meeeee 88‌).[‌88‌] Mee eeeeeeeeee eeeee eeee eeeeeeee ee eee eeeeeeeeeeeeee eee eeee eeeee ee ee eeeeeeee ee eeee; eee eeeeeee, eee eeeeeeeeee eeee eee eee eeeeeeeee ee eeeeeee ‌88‌ eee 88%. Mee eeeeeeee ee eeeeeeeee ee eee eeeeeeeeee ee eeee eeeeeee eeee eeee eeeeeeee (eee ‌Meeeee 88‌, Meeeeee ‌88.8.8.8.8‌).

‌Meeeee 88‌ Meeeeeeee-Meeeeeeee Meeeeeeee ee 8,8-Meeeeeeeeeeeeeee eeee Meee(MM) Meeeeee[‌88‌]

Mee eeeeeeeeeeee ee eeeeeeee eeeeeee eeee eee eeeee eeeee eeeee eeeeee ee eeeeeeeee eeeeeee ee eeeeeee ee eee eeeeeeee ee eeeee-eeeeee(eeee)eee(eeeeeeeeeeeeeeeeee)eeeeee eeeeeeeee[‌88‌] eee eeee eeeeeee ee eee eeeeeeeee ee eeeeeeeee-8-eeeeeeeeeeee eee -8-eeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeee-Meeeeeeee Meeeeeeeeee ee Meeeeeeeeeeeeeeeeeeeee eeee Meeeee Meeeeeee[‌88‌]

Mee eeeeeeeee-eeeeeeeee eeeeeeee ee eeee eeeeeeee eeee eeee(MM) eeeeeee ee eee eeeeeeeeeeeeeeeee eee eeee eeeeeeeeeeee eeeeeee ee eee eeeeeeeeee ee 8-eeeee-8-eeeeeeeeeeeee-8-eeeee (‌88‌) eeee 8-eeeee-8-eeeeeeeeeeeeeeeeeeeee (‌88‌) ee e eeeee-eeeeeeee eeeee, eeeeeeeeeeeee eee eeeeeee eeeeeeeeeeeee ee eeee eeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meeee-8-eeeeeeeeeeeeeeeeeeeee[‌88‌]

Mee eeeeeeeee ee eeeeeeeeeeee eeeeeee eeeeeeeee ee ee eeee eeeeeeeee eeeeee–eeeeeeeeeeeeeeeeee eeeeeeeee [Me(MMe8)e] eeee eeeeee eeeeeeee ee eeeeeeeeeeeeeeeeeeee eeeeeeee eee eeee eeee eeeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (‌88‌), Meee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (‌88‌), eee Meee[8,8-e]eeeeeeee-8-eeeeeeeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

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

M eeeeeee ee eee eeeeeeeeeeeee ‌88‌ ee ‌88‌ (8.8 e, 8.8 eeee) eee MeMM (8.8 e, 88.8 eeee) ee MMM (8 eM), ee e eeeeeee ee eee eeeeeeeeeeeee ‌88‌ (8.8 e, 8.8 eeee) eee MeMM (8.8 e, 88 eeee) ee MMM (8 eM), eee eeeeeeee eeee eeeeeeee eee eeeeeee eeeee (8 e eee ‌88‌, 8 e eee ‌88‌, eee 8 e eee ‌88‌). Meeee eeeeeee, eee eeeeeee eee eeeeeee eeee 88% ee MMM eeee (88 eM), eeeeeeeee eeee MMMe8, eee eee eeeeeee eee eeeee (MeMM8). Mee eeeeeee ee eee MMMe8 eeeeeee eee eeeeeeeeeee ee Me8M, eeeeee eeee M8M, eeeee (MeMM8), eee eee eeeeeee eeeeeeeeee. Meeeeeeeeeeeeeeee (Me8M) eeee eee eeee eeeeeeee; eeeee: 88% (‌88‌); 88% (‌88‌); 88% (‌88‌).

8-Meeee-8-eeeeeeeeeeeeee-8-eeeeeeeeeeee (‌88‌, M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

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

M eeeeeee ee 88% MeMM (8.888 e, 8.8 eeee) eee 88% MeMM (8.888 e, 8.8 eeee) ee eee MMM (8 eM) eee eeeeeee eee eeeeee ee ee. 888°M. Me eee eeeeeeeee eeeee eeee, eee eeeee 8-eeeee-8-eeeeeeeeeeeee-8-eeeee (888 ee, 8.8 eeee) ee eeeee eeeeeeee, eee eee eeeeeee eee eeeeeeeeee ee 888–888°M eee 8 e. Meeee eeeeeee ee ee, eee eeeeeee eee eeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeee eeee eeee ee MeMM (8.88 e ee 88 eM M8M). Mee eeeeeee eee eeeeeee eee 88 eee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee 88% ee MeMM (88 eM) eee eeee eeee M8M. Mee eeeeeee eee eeeeeeeeee eeeee eeeeee (MeMM8). Mee eeeeeee eee eeeeeeee ee eeeeeeeeeee ee 888°M eeeee eeeeeee eeeeeeee; eeeee: 888 ee (88%); ee 888–888°M.

8-Meeee-8-eeeeeeeeeeeeeeeeeeeee (‌88‌):[‌88‌]

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

M eeeeeeee eeeeeee ee MMM (88.8 ee), M8M (888 eM), 8-eeeee-8-eeeeeeeeeeeee-8-eeeee (‌88‌; 8.88 ee, 88.8 eee), Me(MM)8 (8.88 ee, 88 eee), eeee (88.8 e, 8.888 eee), eee Me8(eee)8 (88.8 e, 8.888 eee) eee eeeeee ee 888°M eee 88 e eeeee M8. MMM eee MMMM (Meeeee Meeeeeeeee M8 MM/MM eeeeee) eeeeeeee eeeeeeeee eeeeeeee eeeeeeeeeee ee ‌88‌ (<8.8%) eeeee 88 e, eee eee eeeeeee eee eeeeee ee 88°M. Mee eeeeeee eee eeeeeeeee eeeeeee eeee eee. ee MM8Me/eeeee MM8MM/M8M eeee (8:8:8, 88.8 M) eeee 8 e. Mee eeeeee eee eeeeee ee −8°M eeee 8.8 e eee eeeeeeee. Mee eee eeeeeeeeeee eeeee eee eeeeee eeee eee. ee MM8Me/MM8MM/M8M eeee (8:8:8, 88.8 M) eee M8M (88 M) ee 8°M. Mee eeeee eee eeeee eeeee e eeeeee ee M8, eeeeee eeee eeeeeee (88.8 M), eee eeeee eeeee e eeeeee ee M8 ee eeeeeee eee eeeeeee; eeeee: 8.88 ee (88%); ee 888–888°M; Me 8.88 (e-MeMMe/eeeeee 8:8).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8-8, 8888.
• 8.Meeeee-Meee, (8888) M 8-8, 8888.
• 8.Meeeee-Meee, (8888) M 8e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 888.
• 8.Meeeee-Meee, (8888) M 8e, 888.
• 8.Meeeee-Meee, (8888) M 8e8, 888.