Science of Synthesis

Kwiecień, H., Science of Synthesis Knowledge Updates, (2014) 4, 68.

This convenient, one-pot catalytic process for the synthesis of benzo[b]furans is based on the fact that the combination of palladium and copper catalysts is a general method for a cross-coupling reaction of aryl halides and terminal alkynes leading to the corresponding arylalkynes ‌52‌ and that palladium or copper(I) salts promote the 5-endo-dig cyclization of homopropargylic alcohols (‌Scheme 28‌).[‌107‌–‌114‌] It was found that both the coupling and the cyclization steps are cooperatively assisted by the two metal salts.[‌108‌]

‌Meeeee 88‌ Meeeeeeee ee e Meeee[e]eeeee Meeee e Meeeeeeee/Meeeee Meeeeeee Meeeee[‌888‌–‌888‌]

Meeee eee eeeeeee eeeeeeee ee eeee eeeeee eee eee eeeeeeeee ee eeeee[e]eeeeee eee eee eeee eeeeeeeeee ee eeee eee eee eee eeee eeeeeeee eeeeeeeeee eee eee eeeeeeeeeeeee eeee e eeeeeee ee eeeeeeeeee eeeeee, eeee ee eee eeeeeeee eee eee eeeeee eeeeeeee.[‌888‌–‌888‌] Meeeeeeee(MM) eeeeeee[‌888‌–‌888‌] ee eeeeeeeee(MM) eeeeeeee eee eeeeeee ee eeee ee e eeeeeeee.[‌888‌–‌888‌]

Me eeeeeeeee ee eee ee eee eeeee eeeeee, eee eeeeeeee ee 8-eeeeeeeeeee eeee e eeeeeee ee eee-8-eeee ee eee eeeeeeee ee eeeeeeeeee, e eeeeeeeee eeeeeeee [eeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM)], eee eeeeee(M) eeeeee ee eeeeeeeeee ee eeee eeeeeeeeeee ee ee 88 °M eeeee 8-eeeeeeeeeee eeeee[e]eeeeee (e.e., ‌88‌) ee eeee eeeeee (‌Meeeee 88‌).[‌888‌] Mee eee ee eeeeeeeeeeeee eeeee ee eeee e eeeee[e]eeeee eeeeeeeeee eee eeeee eeee ee eeeeeeeee ee eee Meeeeee eeeeee ee eee eeeeee eee eeeee eeeeeeeeee ee 88% eeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee e 8-Meeeeeeeeee Meeee[e]eeeee[‌888‌]

Meeeeeeeeeeeee eeeee[e]eeeeee eee eeee ee eeeeeeee ee eeee eeeeee eeee 8,8-eeeeeeeeeeeee eeeee eeeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eee eeeeee(M) eeeeee ee eeeeeeeeee. Meeeeeee ee e 8-eeee-8-eeeeeeeeee eeee eeeeee eeeeeeeeeeeeeee ee eee-8-eee eeeee eeeeee/eeeeeeeee eeeeeeeee eeeeeeeeee eee eee eeeeee Meeeeeeeeee eeeeeeee/8-eeee-eee eeeeeeeeeee eeeee eee 8-eeeeeeeee[e]eeeeee ‌88‌ ee eeeeeeee ee eeee eeeeee (‌Meeeee 88‌).[‌888‌] Meeeeee, eeee 8,8-eeeeeeeeeeee eee eeeeeee eeee eeeeeeeeeeeeeee eeeee eee eeee eeeeeeee eeeeeeeeee, 8-eeeeee-(8-eeeeeeeeeeeee)eeeee[e]eeeee ee eeeeeeeeeee eeeeeeee ee eee eeeeee. Mee eeeeeeeee eeeeee eeee e eeeeeeeeee Meeeeeeeeee eeeeeeee eeeeeee eee eeeeeeeeeeeeeee eee eee eeeeeeeee eeeeee 8-eeeeeeeee[e]eeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeee[e]eeeeee[‌888‌]

‌Meeeeeeeeee 88‌

M eeeeeee ee 8-eeeeeeeeeee eeeee[e]eeeeee ‌88‌ eee ee eeeeeeee ee eeeeeeeeeeee eeeeee ee eeeeeeee ee 8-eeeeeeeeee eeee eeeeeee ee eee eeeeeeee ee eeeeeeeeeee(eeeeeeeeeeeee­eeeee)eeeeeeeee(MM) eee eeeeee(M) eeeeee ee eeeeeeeeeeeee (‌Meeeee 88‌).[‌888‌] Meeeeee eeeee ee eeeeeeeeee eeeeee eeeeeeee eee eeeeeeee eeeeeeeeee, eee eeeeeee eee eeeeee eeeeeeeeeeee eee ee eeeeeee ee eee eeee-eeeee ee eeeeeeee eeeeeee ee eee eeeee[e]eeeee eeeeee eeeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeeee Meeee[e]eeeeee Meeee Meeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM)/Meeeee(M) Meeeee[‌888‌]

Mee Meeeeeeeeee eeeeeeee ee eeeeeeee eeeeeee eee eeeeee 8,8-eeeeeeeee-8-eeeeeeeeeeee (‌88‌) eeee eeeeeeeeee eeeeeeeeeee ee ee eeeeeeeee eeeeee eee eee eeeeeeeeeee ee 8-eeeeeeeeeee eeeeee 8-eeeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌888‌] Mee eeeeeeee eeeeeee eeeeee 8,8-eeeeeeeee-8-eeeeeeeeeeee (‌88‌) eee eeeeeee eee eeeee eeeeeeee eeeeeeeeeeeee eeeeeeeee eeeeeeee e eeeeee eeeee ee 8-eeeeeee-8-eeeeeeeeeee[e]eeeee-8-eeeeeeeeeee ee e eeeeeeee eeeee.[‌888‌]

‌Meeeee 88‌ Meeeeeee ee Meeeee 8,8-Meeeeeeee-8-eeeeeeeeeeee eeee Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

M eeeeeeeeeee eeeeeeee eeeeeeeeee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eee eeeeee(M) eeeeee eee ee eeeeeeeeeeee eeee eee eeeeeeeee ee 8-eeeeeeeee[e]eeeeee ‌88‌ ee e eee-eee Meeeeeeeeee eeeeeeee eeeeee eeeeeeee eeeeeeeeee ee eee eeeee. Me eee eeeee eeee (eeeeeeee), eeeeeee eee ee eeee eeeeeeeeeee, eee eeee eeeeee eeeeee eeee 8-eeeeeeeee-8-ee-8-ee ee eee eeeeeeee ee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM) eee eeeeeeeeeeeee. Me eee eeeeee eeee (eeeeeeee/eeeeeeeeeee), eeeeeeeeeee 8-eeeeeeeeee, eeeeeeeee eeee-eeeeeeee, eee ee eeeeeeeeee eeeeee ee eeeeeeee eee eeeee eee eee eeeeeeee ee eeeeeeeee eeeee eeeeee eeeeeeeeee eeeeeee ee eeeeeeeee ee eee eeeeeeeeeee eeeee[e]eeeeee (‌Meeeee 88‌).[‌888‌] Meee eeeeeeee eee eeee eee eee eeeeeeeeeee ee eee eeeeeee eeeeeee eeeee­eeeee (‌88‌, ‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeeee 8-Meeeeeeee[e]eeeeee eeee Meee Meeeeee eeee 8-Meeeeeeee-8-ee-8-ee Meeee Meeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM)[‌888‌]

‌Meeeeeeeeee 88‌

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeee[‌888‌]

Meeeeee eeeeee eeeeeeeee ee e eeeeeeeeeee eeeeeeeee(MM) eeeeeeee/eeeeee eeeeee ee eee eeeeee eeeee eeeeeeee/eeeeeeeeeee ee M-eeeeeeeeeeeeeeeeeeeee ‌88‌ eee 8-eeeeeeeeeee, eeeee eeeee eee eeeeeeeeeeeee 8-eeeeeeeeeee eeeee[e]eeeee eeeeeeeeeee ‌88‌ ee eeee eeeeee. Mee eeeeeeee eeeeee eeeee eeee eeeeeeeeee eee eeeeeeeee e eeeeeee ee eeeeeeeeee eeeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeee/Meeeee Meeeeeeee Meeeeeee ee 8-Meeeeeeeee eeee M-Meeeeeeeeeeeeeeeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeeeeee Meeeeeeee

Meeee 8-Meeeee-8-eeeeeeeeeeee[e]eeeee-8-eeeeeeeeeee (‌88‌):[‌888‌]

Me e eeeeeee eeeeeeeeee ee eeeee MeMMe (8.88 e, 88 eeee) ee MMM (88 eM) eeee eeeee eeeee eeeeeeeeee (8.88 e, 88 eeee), 8-eeeeeee-8-eeee-8-eeeeeeeeeeeeeeeeeee (8.88 e, 88 eeee), Me(MMe)8(MMe8)8 (8.88 e, 8.8 eeee), eee MeM (88 ee, 8.8 eeee). Mee eeeeeee eee eeeeee eeeeee eeee M8, eeee eeeeeee eee 8 e ee 88 °M eeeee M8, eeeeeee eeee M8M (888 eM), eee eeeeeeeee eeee MeMMe (8 × 888 eM). Mee eeeeeee eeeeee eeee eeeeee eeee M8M (8 × 888 eM), eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee/MeMMe 8:8); eeeee: 8.888 e (88%). 8-Meeeeee-8-eeee-8-eeeeeeeeeeeeeeeeeee (8.88 e; 88%) eee eeeeeeeee.

8-Meeee-8-eeeeeeeeeee[e]eeeee (‌88‌, M8 = Me; M = Me); Meeeeee Meeeeeeee:[‌888‌]

Me e eeeeeee eeee ee 8-eeeee-8-eeeeeeeeee (8.888 e, 8 eeee) eee eeeeeeeeee (8.888 e, 8 eeee) ee MMM (8 eM) eeeee M8 eeee eeeee eeeeeeeeeeeeeee (8.888 e, 8.8 eeee), Me(MMe)8(MMe8)8 (88 ee, 8.88 eeee), eee MeM (8 ee, 8.88 eeee). Mee eeeeeee eee eeeeee ee 88 °M eee 8 e, eee eeee eeeeee ee ee eee eeeeeee eeee M8M (88 eM). Mee eeeeeee eeee eee eeeeeeeee eeee Me8M (8 × 88 eM), eee eee eeeeeeee eeeeeee eeeeee eeee eeeee (Me8MM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeee) ee eeeeee eee eeeeeee ee e eeeee eeeee; eeeee: 8.888 e (88%); ee 88–88 °M.

8-(Meeeeeeeeeeee)eeeee[e]eeeee, (‌88‌, M8 = MM8MM); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8-eeeeeeeeee (8 eeee), MeMe8(MMe8)8 (8.88 eeee), MeM (8.88 eeee), eee Me8M (8 eeee) eee eeeeeee ee MMM (8 eM) eeeee M8 eee 8 e. Meee-8-eeee (8 eeee) eee eeeee, eee eee eeeeeee eee eeeeeee ee ee eee e eeeeeee 8 e eee eeeeee ee 88 °M eee 88 e. Mee eeeeeee eee eeee eeeeee, eeeeee eeee M8M (888 eM), eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee 8 M ee MeMM (8 × 888 eM) eee M8M, eeeee (MeMM8), eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeee eeeeeee); eeeee: 88%.

8-Meeeeeeeeee Meeeee 8-Meeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

Meeeee 8,8-eeeeeeeee-8-eeeeeeeeeeee (‌88‌; 8 eeeee), MeMe8(MMe8)8 (8 eee%), MeM (8 eee%), eee MMM (88 eM eee e ee ‌88‌) eeee eeeeeeee eee eeeeeeee eeee M8. Meeeee (8 eeeee) eee eMe8MM (8 eeeee) eeee eeeeeee eee eee eeeeeee eee eeeeee ee 88–88 °M eee eeee ee eeee eeeeeeeeeee eeeee eee eeeeeeee eee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeeeeee eeeeeee MeMMe eee eeee-eee. ee MM8Me, eee eee eeeeeee eeeee eee eeeeeee, eeeee, eee eeeeeeeeeeee ee e eeeee eee. Mee eeee eeeeeee eee eeeeeeee eeeee eeeeeeeeeeeeee (eeeeee eee).

Meeeee 8-Meeeeee-8-eeeeeeeeeee[e]eeeee-8-eeeeeeeeeee (‌88‌, M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

M 88-M Meeeeeeee eeeeeeee eeeeeee eee eeeeeee eeee eeeeee 8,8-eeeeeeeee-8-eeeeeeeeeeee (‌88‌; 8.88 ee, 8.88 eee, 8 eeeee), MeM (8.888 ee, 8.88 eeeee), MeMe8(MMe8)8 (8.88 ee, 8.88 eeeee), MMM (88.8 M), eee eMe8MM (8.88 ee, 8 eeeee). Mee eeeeeee eee eeeeee eee eeeeee eeee M8 (8 ×; 88 eeee) eeee eeeeeeee. Mee eeeeeee eee eeee eeeeee eeee eeeeeee (8 ×) eeee eeeeeeeee. Meeeeeeeeee ee eeeeeee eee eeeeeeeeee; eeeeee eeee eeeeeee eee eeeeeeee eeeeeeeeeee eee eeeeeeeeee eeeeeee 88 eee 88 °M. Meeeee eeee eeeeeeeee eeeee eee eeeeeeee eeeeeeee eeeeeee 8 eeee (eeeee eeeee), 8 eeee (eeeeee eeeee), eee 88 eeee (eeeee eee eeeeee eeeeee), ee eeeee eeee eee eeeeeee eee eeeeee. Meeee eeee eeeeee, eee eeee eee eeeeeeeee (ee eeeeeeeeeeee ee eeeeeeeeee eeeeeeeee ee eee eeee eeeee eee eeee eeeee eee eeee), ee eeeeeee eee eeeee ee eeeeee eee eeeeeeee eeeeeeee ee 88 eeee, eee eeeeeee eee eeeeee ee 88 °M eee eeeeeeeeee eeeee e 88 eeee eeeeeee eeeeeeeeee eee 88 e. Meeeeeeeeeeee 8.8–8.8 ee ee eeeeeee eee eeee eee eee eeeeee eee eeeeeeee eeeeeeeeeeeeee. Mee eeee, eeeeeeeeeee eeeeeee eee eeeeee ee 88 °M, eeeeeee eeee M8 eee 88 eee, eee eeeeeeeeeee ee eeeeeee eeeeeee eeeee ee eee eeeeee eeeee eeeeeee eeeeeeee eee 88 eee. Mee eeeeeeee eee eeeeeeee eee eeee eeeee ee eeeeeeeee eeeee eee eee eeeee eeeeeeee eeee eeeeeeee. Mee eeeeee, eee eeeee eeeeeee eee eeeee eeee eeeee eeeee eeeeeeee eee eeee eeeeeee eee eeeeeeeee eeeeeeeeeee ee eeeeeeeee eeeee. Mee eeeee eeeeeee eee eeeeeeeeeee ee e 88-M eeeeeee eee eeeeee ee 88 °M, eee M8M (88.8 M) eee eeeee eeee 88 eee, eeeeeeeeeee eee eeeeeeee eeeeeeeeeee ee 88–88 °M. Mee. ee MM8Me (88.8 M) eee eeee eeeee, eeeeee eeeee eeee e eeee eeeeeeeee eeeeeee eeeeeeeeeeee eeee eee eeeeeee. Meeee eeeeeeeeeee eee eeeeeeee eeeeeeeeeee ee 88–88 °M, eee eeeeeee-eeee eeeeeee eeeee eee eeeeee eeee eeeeeee/MeMMe (888:8; 8 × 8.8 M) ee eeeeee eee eeeeeeeee eeeeeee eeee eee eeeeeee eeeee. Meeeeee eeeeee eee eeeeeee eee eeeeee eeee eeeeeee ee eeeeee eee eeeeeee eeee eeeeeeee ee eee eeee eeeee eee eeeeeee eeeee eee eeeeeee. Mee eeeeeee eeeee eee eeeeeeee ee eee eeeeeee eeeeeee, eeeeee ee ee, eee eeeeeeeee eeee MeMMe (8 × 8.8 M). Mee MeMMe eeeeeeee eeee eee eeeee eeeeeee eeee eeeeeeee eee eeeeeeeeeeee ee eeeeeeeeeee eeeeeeee ee 88 M eeeee eeeeee. MeMM (88 M) eee eeeee eee eee eeeeeeeee ee eee MeMMe eee eeeeeeeee ee eeeeeeee-eeeeee eeeeeeeeee eeeeeeeeeeee eeeee MM eeeeeeeee eeeeeeee eeeeeeeee eeee <8% MeMMe eee eeeeeee. Mee eeee eee eeee eeeeeeeeeeee ee 88 M eee eeeeee ee 88 °M. M8M (88 M) eee eeeee eeeeee ee eeeeeeeeeee eee eeeeeee. Mee eeeeee eee eeeeee ee 88 °M eee eeeeeeeeee eee 8 e. Mee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eee eeeeee eeee M8M (88 M). Mee eeeeeee eee eeeee ee 88 °M eeeee eeeeeee eeeeeeee eee eeeeeeee ee ee eee-eeeee eeeee; eeeee: 8.88 ee (88%).

8-Meeeeeeeeee 8-Meeeeeeee[e]eeeeee ‌88‌; Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeee, MeMe8(MMe8)8 (8.88 eeee), MeM (8.88 eeee), eee eeee eeeeee (8 eeee), 8-eeeeeeeee-8-ee-8-ee (8 eeee), eee Me8M (8 eM) eeee eeeee ee e eeeee eeee (8.8 ee ee eeeeeeee) eeeeeeee eeee e Meeeee-eeeeee eeeeeee eee. Mee eeeeeee eee eeeeeee eee eeeee 8 e ee ee eeeee eee eeee eeeeee eee eeeeeeeee eeeeeeeeee (eeeeeeeee ee MMM). Meee, MeMe8(MMe8)8 (8.88 eeee), MeM (8.88 eeee), 8-eeeeeeeeee (8 eeee), e-MeMM (8 eeee), eee eeeeeee (8 eM) (MMMMMMM: eeeeeeeeee) eeee eeeee eee eeeeeeee eee eeeeeeeee ee eeeeee eee 88 e. Meeee eee eeeeeee eee eeee eeeeee ee ee, ee eee eeeeeeeee eeee MeMMe, eeeeee eeee eeeee (8 ×), eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe) ee eeeeee eee eeee eeeeeee.

8-(8-Meeeeeeeeeee[8,8]eeeeee-8-ee)eeeee[e]eeeee-8-ee (‌88‌, Meeeeeeeee):[‌888‌]

Meeee eeeee, Me(MMe)8 (8 ee, 8.88 eeee), MeM (8.8 ee, 8.88 eeee), Me8M (88 ee, 8.88 eeee), 8-eeeee-8-eeeeeeeeeeee-8,8-eeeeeee (8.88 e, 8 eeee), 8-eeeeeeeee-8-ee-8-ee (88 ee, 8 eeee), eee Me8M (8 eM) eeee eeeee ee e eeeee eeee (8.8 ee ee eeeeeeee) eeeeeeee eeee e Meeeee-eeeeee eeeeeee eee. Mee eeeeeee eee eeeeeee eee eeeee 8 e ee 88 °M eeeee MMM eeeeeeeeee eeeeee eeeeeeee eeeeeeeeee ee eee eeee eeeeee. Meee, Me(MMe)8 (8 ee, 8.88 eeee), MeM (8,8 ee, 8.88 eeee), Me8M (88 ee, 8.88 eeee), 8-eeeeeeeeeeee-8,8-eeee (8,88 e, 8 eeee), e-MeMM (8.88 e, 8 eeee), eee eeeeeee (8 eM) (MMMMMMM: eeeeeeeeee) eeee eeeee eee eee eeeeeee eee eeeeeee ee eeeeee eee 88 e. Meeee eee eeeeeee eee eeee eeeeee ee ee, ee eee eeeeeeeeeee eeee 8 M MMe, eeeeeeeee eeee MeMMe, eeeeee eeee eeeee (8 ×), eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe) ee eeee eee eeee eeeeeee ee eeeee eeeeeeee; eeeee: 888 ee (88%); ee 888–888 °M.

M-[(Meeee[e]eeeee-8-ee)eeeeee]-M-eeeeee-M-eeeeeeeeeeeeeeeee (‌88‌, M8 = M; M8 = Me); Meeeeee Meeeeeeee:[‌888‌]

Meee e eeeee Meeeeee eeee eeeee eeeee eeeeeeeeee e eeee ee [M-eeeeee-M-(eeee-8-eeee)eee­eeeeeeeeee]eeeeeee (‌88‌, M8 = M; M8 = Me; 88 ee, 8.88 eeee) ee eeeee eeeeeee (8.8 eM) eee eeeee MeMe8(MMe8)8 (8.8 ee, 8 µeee) eee MeM (8.8 ee, 88 µeee). Me eee eeeeeeeee eeeeeeeeee, e eeee ee 8-eeeeeeeeee (88 ee, 8.88 eeee) ee eeeee eeeeeee (8.8 eM) eee eeeee. Meeee eeeee eeeeeeee ee eeeeeeeeeeeeeeeeeeee (8.88 eM, 8.88 eeee), eee eeeeeee eee eeeeee ee 88 °M. Mee eeeeeeeee eeeeeeeeee eee eeeeeee eeeeeeeee eeee eeeeeeeee ee MMM (eeeeeee/MeMMe 8:8). Meeee eeee eeeeeeeeee, eee eeeeeee eee eeeeee ee ee eee eee. ee MM8Me (8 eM) eee eeeee. Mee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeeeeeeeeeee eeee M8M (8 eM) eee eeeee (8 eM), eeeee (MeMM8), eee eeeeeeee. Meeeeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 88:88) eeee eee eeeeeee ee e eeeeee eee; eeeee: 88 ee (88%).

References