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2.1.3.1.1.1 With Aryl Halides

DOI: 10.1055/sos-SD-208-00133

Ahmad, O. K.; Movassaghi, M.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132195.

One of the first methods utilizing the Ullmann reaction with broadly applicable conditions for the synthesis of N-arylhetarenes was reported by Buchwald and co-workers.[‌5‌] The transformation uses copper(I) trifluoromethanesulfonate as the catalyst source, and 1,10-phenanthroline and dibenzylideneacetone as additives (Scheme 1). Both electron-rich and electron-deficient aryl halides can be used as coupling partners. Typically, aryl iodides are coupled at lower temperatures and require shorter reaction times compared with aryl bromides. The yields of products such as 1 are generally 90% or higher. Lower yields are observed for aryl halides with ortho substituents (vide infra).

Meeeee 8 Meeeeee Meeeeeee ee Meeeeeeeee eeee Meee Meeeeee Meeeeeeee ee Meeeee(M) Meeeeeeeeeeeeeeeeeeeeeeee/Meeeeeeeeeeeeeeeeeee/Meeeeeeeeeeeee[‌8‌]

Meeeeeeeeee 8

M8 M8 Me8 M Meee (e) Meeee (%) Mee
M M 8-e-MeM8M8 M 88 88 [‌8‌]
M M 8-M8MM8M8 M 88 88 [‌8‌]
M M 8,8-Me8M8M8 Me 88 88 [‌8‌]
Me M Me M 88 88e [‌8‌]
M M 8,8-Me8M8M8 Me 88 88 [‌8‌]
(MMMM)8 8,8-Me8M8M8 M 88 88 [‌8‌]

e Meeeeeee eeeee ee 8-eeeeee-8-eeeeee-8M-eeeeeeeee (8, M8 = Me; M8 = M) eee 8-eeeeee-8-eeeeee-8M-eeeeeeeee (8, M8 = M; M8 = Me); eeeee 8.8:8.

Mee eee ee eeeeee(M) eeeee eeee e eeeeeeeeeeeeee eeeeee eee M-eeeeeeeee ee eeeeeeeeee eeee eeee eeeeeee eee eeeeeeee eeeeeeee ee eeeeeeee eee eee eeeeeeeee ee eeeeeeeeeee eeeeeeeeee 8 eeeee eeee eeeeeeeeee (Meeeee 8).[‌8‌] Meeeeee eeeeeeee eee eeeeeeeeeeeeee eeeeeeeeee eee eeee eeeeeee eee eeeeeeeeeee ee eeee ee eeeeeeeee eeeeee. Mee eee ee eeeeeeeeee eeee eeeee eeeeeeeeeeee eeee eee eeeeeeeee eeeeee eee eeeee. Me eeeeeeee, eeeeeeeeeee eeeeeeee eee eeeeeee eee ee eeee, eee eee eeeeeee eeeeeeee eeeeeeee eee ee eeeeeeee ee eeee eeeeee.

Meeeee 8 Meeeee(M) Meeee/Meeeeeeeeeeeee Meeeeeeee M-Meeeeeeee ee Meeeeeeeee eeee Meee Meeeeee[‌8‌]

Meeeeeeeeee 8

M8 Me8 M Meeee (%) Mee
M Me M 88 [‌8‌]
M 8-M8MM8M8 M 88 [‌8‌]
M 8-MMM8M8 Me 88 [‌8‌]
M 8-MMMM8M8M8 M 88 [‌8‌]
M 8-Mee Me 88e [‌8‌]
M 8-MeM8M8 Me 88 [‌8‌]
Me 8-e-MeM8M8 Me 88 [‌8‌]

e MMM eeee ee eee eeeeeee.

Meeeeee eeeeeee eeee eeeeeeee eeeeeeee eeeeeeeeee eeee eee eeeeeeeeee ee e eeeeeee ee eeeeeeeee.[‌8‌,‌8‌] M-Meeeeeeee ee eeeeee eeee eeeeeee ee eeee eeeeeeee eeee eeeeeeee eeeeeeeeeeee 8, eeeeeeeee eeeeeeee, eeeeeeeee, eeeeeeeee, eeeeeeeeee, eee eeeeeeeee, ee eeeeeeeeeeee eeeeeeeee ee eeee eeeeeeee 8 ee eeee eeeee (88–888%) eeee eeeeeeeee eeeeeee eeee eeeeeee eeeeeee eee eeeeee(M) eeeeee (Meeeee 8). Mee eeeeeeee eeeeeeeeee eee eeeeeeee ee e eeeeeee ee eeeeeeeeee eeeeee, eeee ee eeeeee eee eeeeeee.

Meeeee 8 Meeeee(M) Meeeee/Meeeeee Meeeeeeee M-Meeeeeeee ee Meeeee eeee Meee Meeeeee[‌8‌]

Meeeeeeeeee 8

Me8 Me8 M Meeee (%) Mee
8M-eeeeee-8-ee 8-Me8MM8M8 Me 88 [‌8‌]
8M-eeeeeee-8-ee 8-MeMMM8M8 Me 88 [‌8‌]
8M-8,8,8-eeeeeee-8-ee 8-MeMM8M8 M 88 [‌8‌]
8M-eeeeeeee-8-ee 8,8-Me8M8M8 M 88e [‌8‌]
8M-eeeeeee-8-ee 8-MeMM8M8 M 88e [‌8‌]
Me Me M 88 [‌8‌]

e 8,88-Meeeeeeeeeeeee eee eeee ee eeeeee.

e Meeeeee eeeeeeeeeeeee eeeee (8-eeee-8M-eeeeeeee/8-eeee-8M-eeeeeeee) 88:8.

Meeeeeeeeeeeee eeeeeeeee ee 8,8,8-eeeeeeeee ee e eeeeeeeeeee eeeeeeeeeeeeee. M eeeeeeeee-eeeeeeee eeeeeeee eeeeeeeee ee Mee eee ee-eeeeeee eeeee eeeeee(M) eeeeeeee eee eeeeeee eeeeeeee eeeeeeeee eeeeee ee e eeeeeee ee eeeeeee eeeeeeeeeee 8-eeee-8M-8,8,8-eeeeeeeee ee eeee eeeeee (Meeeee 8).[‌8‌] Meeeeeeeeeeee eeeeeeeee eeeeeeeeeee eeeeeee eee 8-eeeeeeee eeeeeeee 8. Meeeeeeeeeeeeee eeeeeeeee, ee eee eeeee eeee, eeeeee eeee eeeee eeeeeeeeeeeeeeee; eee eeeeeee, eee eee ee 8-eeeeee-8,8,8-eeeeeeee (8, M8 = Me; M8 = M) eeeeeee eee 8- eee 8-eeeeeeee eeeeeeee ee 88 eee 88% eeeeee, eeeeeeeeeeee. Meeeeeee-eeeeeeeee eee eeeeeeee-eeee eeee eeeeeee eee eeeeee eeeeeeeeee eee eeeee eeeeeeeeee. Meeeeee, eeee eeeeeeee ee eee eeeeeee eee eeeeeee eeeeeeee eeeeeeee ee eeeeeeeeeeeee eeeeee eeeeee.

Meeeee 8 Meeeeeeee-Meeeeeee 8-Meeeeeeee ee 8,8,8-Meeeeeeee[‌8‌]

Meeeeeeeeee 8

M8 M8 Me8 Meeee (%) Mee
Me Me Me 88 [‌8‌]
Me M Me 88 [‌8‌]
8-eeeeeeee M(Me)MM8 Me 88 [‌8‌]
Me Me 8-M8MM8M8 88 [‌8‌]
Me Me 8-eeeeeee 88 [‌8‌]
Me M(Me)MM8 8-eeeeeeee 88 [‌8‌]

Mee eee ee-eeeeeeeʼ eeeeee-eeeeeeeee M-eeeeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeeee eeeeeeee eeeee eeee eeee eeeeeeeeee ee eee eeeeeee ee ee eeeeeeeeee eeeeee (Meeeee 8).[‌88‌] Meeeeee eeee eeeee eeeeeeeee eeeeeee eeeeeee ee eeee eeeeeeeeeeee (eeeeeeeee eeeeeee eeee 888 °M), eeee eeeeeeeeeeeeee eeeeeeee eeee eeeeeeee eeeeeeee eeeeeeeeeeee. Mee eeeeeeee eeeeeeeee e eeeeeee ee eeeeeeeeee eeeeee eeeeeeeee eeeeeeeeeee eeeeeee eeeeee, eeeeeeeee, eee eeeeeeee.

Meeeee 8 Meeeee(M) Meeeee Meeeeeeee M-Meeeeeeee ee Meeeee eeee Meee Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 Me8 Meeee (%) Mee
MM M 8-M8MM8M8 88 [‌88‌]
MM M 8-(MMMMe8M≡M)M8M8 88 [‌88‌]
MM M 8-MMMM8M8 88 [‌88‌]
M M 8-MeMM8M8 88e [‌88‌]
M MMe 8-MeMM8M8 88 [‌88‌]

e Meeeeeee eee ee 88 °M.

Mee eee ee eeeeee(M) eeeeeee eeee e eeeeeeee eeeeee eee eeeeeeeee ee eeeeee eee eeeeeeeee ee Meee eee ee-eeeeeee (Meeeee 8).[‌88‌] Meee eeeeee ee eeeeeeeeeeee eeee eeeeeeee eeeeeeee eeeeeeeeeeee, eeee eeeeee eeeeeeee eeeeeee eeeeeeee eeeee eeeeeeee eeee eeeeeee eeeeeeeee. Mee eeeeee eeee eee eeee eeeeeeeeeeeeee, eeeeeee, ee eee ee eeeeeee eeeeeeeee eeee eeeeeeeeee eeeeeee, eee ee eee ee eeeeeeeeeee ee e eeeeee eeee eeee eeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeeeeeeee.[‌88‌] Meeeeeee-eeee eee eeeeeeee-eeeeeeeee eeee eeeeeee eee eeeeeeee, eeeeeeeee eeeeeee eeeeeee, eeee eeee eeee eeee eeee eeeeee, eee eee eeeeeee eeeeeeee eeeeeeee 8 eee eeeeeeee ee eeee eeeeee (88–88%).

Meeeee 8 Meeeee(M) Meeeeee/Meeeeeee Meeeee Meeeeeeee M-Meeeeeeee ee Meeeee eeee Meee Meeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 Me8 M Meeee (%) Mee
MM M 8-Mee M 88 [‌88‌]
MM M 8-Me-8-M8MM8M8 Me 88 [‌88‌]
MM M Me 88 [‌88‌]
M M 8-MeM8M8 M 88 [‌88‌]
M MMe 8-M8M-8-M8MM8M8 Me 88e [‌88‌]

e Meeeeeee eee ee 888 °M, 88 e.

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

Meeeee 8 Meeeee(M) Meeeee/Meeeeeeeee Meeeee Meeeeeeee M-Meeeeeeee ee Meeeeeeee eeee Meee eee Meeeeee Meeeeee[‌88‌]

Meeeeeeeeee 8

M M8 M Meeee (%) Mee
MM M M 88 [‌88‌]
MM Me M 88 [‌88‌]
MM MM8 M 88 [‌88‌]
MM Me Me 88 [‌88‌]
M M Me 88 [‌88‌]
MM MM8 Me 88 [‌88‌]

M eeeeeeeeeee eeeeeeee ee Me eee ee-eeeeeee eeeeeeee eeeeee ee eeeeeee M-eeeeeeee eeeeeeee, eeeeeeeee, eeeeeeee, eee eeeeeeeee eeeeeeeeeee 88 (Meeeee 8). Meee eeeeee eeeeeeee eeeeee(MM) eeeeeee ee eee eeeeeee ee ee eeeeeeeeee eeeeee.[‌88‌] Mee eeeeee eeeeeeee 88 eeeeeeee eeee eeeeee eeeeeee eeee 88 ee 88%. Meeeeeeee, eee eeeeeeeee 88 eeeeeeee eee eeeeeeeeeeeee eee eee eeee eeeeeee eeeeeeee eee eeeeee eeee eeeeeeeeeee ee eeeeeeeeeeeee.

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

Meeeeeeeeee 8

Me8 M8 Meeee (%) Mee
M 88 [‌88‌]
8M-eeeeeee-8-ee MMe 88 [‌88‌]
8M-eeeeeeee-8-ee Me 88 [‌88‌]
8M-8,8,8-eeeeeee-8-ee Me 88 [‌88‌]
8M-eeeee-8-ee MMe 88 [‌88‌]
8M-eeeeeeeeeeee-8-ee Me 88 [‌88‌]
Me Me 88 [‌88‌]
M 88 [‌88‌]

Meee eee ee-eeeeeeeʼ eeeeeeee eeee e eeeee eeeeeeeee 8-eeeee eeeeee eeee eeeeee(M) eeeeeee ee eee eeeeeeee eeeeee ee eeeeee e eeeeeee ee eeeeeeee eeeeeeeeeeeeeee 88 (Meeeee 8).[‌88‌] Meee eeeeeeeee ee eeee ee eeeeeeee eee ee eeee ee eee eeeeeeee eeeeeeee eeee M-eeeeeeeee 88. Meeeeeee-eeeeeeeee eee eeeeeeee-eeee eeee eeeeeee eee ee eeeeeee, eee eee eeeeee eee eee eee eeeeeeeee eeee eeeeeeee-eeee eeee eeeeeee.

Meeeee 8 Meeeee(M) Meeeeee/Meeeeeeee 8-Meeee Meeeeeeee M-Meeeeeeee ee Meeeee eeee Meee Meeeeee[‌88‌]

Meeeeeeeeee 8

Me8 M8 M Meee (e) Meeee (%) Mee
8M-eeeee-8-ee MM8 Me 88 88 [‌88‌]
8M-eeeeeeeeeeee-8-ee MM8 Me 88 88 [‌88‌]
8M-eeeeeeee-8-ee MM Me 88 88 [‌88‌]
8M-eeeeeee-8-ee MMe Me 88 88 [‌88‌]
8M-8,8,8-eeeeeee-8-ee MM Me 88 88 [‌88‌]
8M-eeeeeeeeeeee-8-ee MM8 Me 88 88 [‌88‌]
8M-8,8,8-eeeeeee-8-ee MM Me 88 88 [‌88‌]
8M-eeeee-8-ee MM8 Me 88 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-(8,8-Meeeeeeeeeeeee)-8M-eeeeeeeee (8, M8 = M8 = M; Me8 = 8,8-Me8M8M8); Meeeeee Meeeeeeee:[‌8‌]

Meeeeeeee (8.8 eeee), 8-eeeee-8,8-eeeeeeeeeeeeeee (8.8 eeee), eee eeeeeee (8.8 eM) eeee eeeee ee e eeeeeee ee MeMMe (8.8 eeee), 8,88-eeeeeeeeeeeeee (8.8 eeee), eee (8.8 eeee), eee Me8MM8 (8.8 eeee) ee e Meeeeee eeeee, eee eee eeeee eee eeeeee eeee eeeee. Mee eeeeeeeee eeee eeeee eeeeeee eee eeeeee ee 888 °M. Meeee 88 e, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee, eee MM8Me8 (88 eM) eee eee. ee MM8Me (8 eM) eeee eeeee. Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee eeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8) ee eeeeee eee eeeeeee eeeeeee ee e eeee eeeeee eee; eeeee: 88%.

8-Meeeeeeeeeeeee 8; Meeeeee Meeeeeeee:[‌8‌]

M eeeeeee ee Me8M (8.888 eeee eee eeee eeeeeee eee 8.88 eeee eee eeee eeeeeeee), eee eeeeee (8.888 eeee eee eeee eeeeeee eee 8.88 eeee eee eeee eeeeeeee), Me8MM8 (8.8 eeee), eee eeeeeeeee (8.8 eeee), eee eeee eeeeee (8.88 eeee, ee eeeee), eee eeee(eeeeeeee eeeeee) (888 ee) eee eeeeee eeee eeeee ee M8. Mee eeee eeeeee (8.88 eeee, ee eeeeee) eee MeMM (8.8 eM) eeee eeee eeeee, eee eee eeeeeee eee eeeeee ee 888 °M. Meeee 88–88 e, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee eee eeeeeee eeee MM8Me8 (88 eM). Mee eeeeeee eee eeeeeeee eeeeeee e eeee ee Meeeee, eeeee eee eeeeee eeee MM8Me8 (88 eM). Mee eeeeeeee eee eeeeeeeeeeee, eee eee eeeeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

M-Meeeeeeeee 8; Meeeeee Meeeeeeee:[‌8‌,‌8‌]

M eeeeeee ee MeM (8.88 eeee), M8MM8 (8.8 eeee), eee eee eeeeeeee 8 (8.8 eeee) ee e eeeeeeeeee Meeeeee eeee eee eeeeee eeee eeeee. Mee eeee eeeeee (8.8 eeee), eeeeeeee (8.88 eeee), eeeee-M8,M8,M8,M8-eeeeeeeeeeeeeeeeeeeeee-8,8-eeeeeee (8.88 eeee), eee eeeeeee (8.8 eM) eeee eeee eeeee, eee eeee eee eeeeee, eee eee eeeeeee eee eeeeee ee 888 °M. Meeee 88 e, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee eee eeeeeee eeee MeMMe (8–8 eM). Mee eeeeeee eee eeeeeeee eeeeeee e eeee ee eeeeee eee, eeeee eee eeeeee eeee MeMMe (88–88 eM). Mee eeeeeeee eee eeeeeeeeeeee, eee eee eeeeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

8-Meee-8M-8,8,8-eeeeeeeee 8; Meeeeee Meeeeeeee:[‌8‌]

M eeeeeee ee MeMe (8.88 eeee), M8MM8 (888 ee, 8.8 eeee), eee eeeeeeee 8 (8.8 eeee), eee eeee eeeeee (8.8 eeee), e-eeeeeee (88 ee, 8.88 eeee), eee eeeee MMMM (8 eM) eee eeeeee ee e eeeeeeeee eeeeee eeeee e M8 eeeeeeeeee ee 888 °M. Meeee 88 eee, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee eee eeeeeee eeee M8M (88 eM). Mee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 88 eM). Mee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

M-Meeeeeeeee 8; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee MeM (88.8 ee, 8.8 eeee), M8MM8 (8.888 e, 8.8 eeee), eee eeeeeeee (8.8 eeee), eee eeee eeeeee (8.8 eeee), eee MMM (8 eM) ee e Meeeeee eeeee eee eeeeee eeee M8 eee eeeeee ee 88–88 °M. Meeee 88 e, eee eeeeeee eee eeeeeee eeee MeMMe (8–8 eM). Mee eeeeeee eee eeeeeeee eeeeeee e eeee ee eeeeee eee, eeeee eee eeeeee eeee MeMMe (88–88 eM). Mee eeeeeeee eee eeeeeeeeeeee, eee eee eeeeeeeee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

M-Meeeeeeeee 8; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee MeMe (8 ee, 8.88 eeee), Me8MM8 (888 ee, 8 eeee), eee eeeeeeee (8.8 eeee, ee eeeee), eee eee eeee eeeeee (8 eeee, ee eeeee) ee e eeeeee eeee eeee e Meeeee eeeee eee eeeeee eeee M8. Mee eeeeeeee (8.8 eeee, ee eeeeee), eee eeee eeeeee (8 eeee, ee eeeeee), eee eeeeee (88 ee, 8.88 eeee), eee MMMM (8.8 eM) eeee eeeee eee eeeeeee eeeee e M8 eeeeeeeeee. Mee eeeeeee eee eeeeee ee 88 °M. Meeee 8 e, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee, eeeeeee eeee MeMMe (88 eM), eee eeeeeeee. Mee eeeeeeee eee eeeeee eeee M8M eee eeeee eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

8-Meeeeeeeeeeeee 8; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee eeeeeeeee (8.88 eeee), MeM (8.88 eeee), 8,8-eee(8-eeeeeee-8-eeeeeeeeeeeee)eeeeeeeeee (8.88 eeee), eee eeee eeeeee (8.88 eeee), MMM (8.8 eeee), MMMM (8.88 eeee), eee M8M (8 eM) ee e eeeeee eeee eeee e Meeeee eeeee eee eeeeee ee 888 °M. Meeee 88 e, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee. Mee eeeeeee eee eeeeeeeee eeee MeMMe (8 × 8 eM), eee eee eeeeeeee eeeeeee eeeeee eeee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

M-Meeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Mee eeee eeeeee (8.8 eeee), eee eeeeeeee 88 (8.8 eeee), eee Me8MM8 (8 eeee) eeee eeeee ee e eeee ee Me(MMe)8•M8M (8.88 eeee) ee MMM (8 eM) eeeee e M8 eeeeeeeeee. Mee eeeeeee eee eeeeee ee 888 °M. Meeee 88 e, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee eee eeeeeee eeee M8M. Mee eeeeeee eee eeeeeeeee eeee MeMMe (8 ×), eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee, eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

M-Meeeeeeeee 88; Meeeeee Meeeeeeee:[‌88‌]

Mee eeee eeeeee (8.8 eeee), eee eeeeeeee 88 (8.8 eeee), eee MMMM (8 eM) eeee eeeee ee e eeeeeee ee MeMe (8.88 eeee), eee eeeeee (8.8 eeee), eee Me8MM8 (88.8 eeee), eee eee eeeeeeee eeeee eee eeeeee eeee eeeee. Mee eeeeeee eee eeee eeeeee ee 88 °M. Meeee MMM eeeeeeee eeeeee eeeeeeee eeeeeeeeeee ee eee eeeeeeee eeeeeeee, eee eeeeeee eee eeeeeee ee eeee ee eeeeeee eeeeeeeeeee, eeeeeee eeee MeMMe, eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeeeee eee eeeeeee eeeeeee.

References