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9.13.5.1.7.2.1.4 Variation 4: Active Methylene Isocyanides and Alkynes under Phosphine Catalysis with Reversal of Regioselectivity

DOI: 10.1055/sos-SD-109-00312

Lubell, W. D.; St-Cyr, D. J.; Dufour-Gallant, J.; Hopewell, R.; Boutard, N.; Kassem, T.; Dörr, A.; Zelli, R., Science of Synthesis Knowledge Updates, (2013) 1, 239.

In addition to the use of stoichiometric base,[‌325‌,‌357‌] catalytic copper,[‌325‌] and phosphines have been effective for promoting pyrrole formation. Phosphines have reversed the regioselectivity in the attack of the electron-deficient acetylene yielding pyrroles ‌234‌ (‌Scheme 85‌).[‌320‌]

‌Meeeee 88‌ Meeeeeeeeee Meeeeeeeeeeeeeee eeee Meeeeeeee Meeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

M8 M8 M8 Meee (e) Meeee (%) Mee
MM8Me Me MM8Me 8 88 [‌888‌]
MM8Me (MM8)8Me MM8Me 88 88 [‌888‌]
MM8Me Me MM8Me 88 88 [‌888‌]
MM8Me 8-MeMM8M8 MM8Me 8.8 88 [‌888‌]
MM8Me 8-M8MM8M8 MM8Me 8.88 88 [‌888‌]
MM8e-Me Me MM8Me 8 88 [‌888‌]
MM8Me Me Me 8 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeee 8-Meeeee-8M-eeeeeee-8,8-eeeeeeeeeeeee (‌888‌, M8 = M8 = MM8Me; M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeeeeeeeeeeeee (88 μM, 8.8 eeee) eee eeeee eee-8-eeeeee (88 μM, 8.8 eeee) eeee eeeee ee e eeee ee eeee (88.8 ee, 88 μeee) ee 8,8-eeeeeee (8 eM) eeeee eeeee, eee eee eeeeeeeee eeee eee eeeeeee ee 888 °M eee 8 e. Meeee eee eeeeeeeeeee ee eeeee eee-8-eeeeee, eee eeeeeee eee eeeeee ee ee, eeeeeeee eeeeeee e eeeee eee ee Meeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:88 ee 8:8) ee eeeeee eee eeeeeee ee e eeeeeeeee eee; eeeee: 88.8 ee (88%); 8M MMM (MMMe8, 888 MMe, δ): 8.88 (ee e, MM, 8M), 8.88 (ee, M = 8.8, 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M), 8.88 (e, M = 8.8 Me, 8M).

References

[320] Meeeee, M.; Meeeeeee, M.; Meeeeeee, M., M. Me. Meee. Mee., (8888) 888, 8888.
[325] Meeee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; ee Meeeeee, M., Meee.–Mee. M., (8888) 88, 888.
[357] Meeeeeeeeeee, M.; Meeeeeeee, M.; Meeee, M. M.; Meeeee, M.; Meeee, M.; Meeeee, M. M.; Meeeeeeee, M.; Meeeeeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888.