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2.1.4.1.3 Palladium-Catalyzed Coupling with Aryl and Hetaryl Halides

DOI: 10.1055/sos-SD-208-00147

Klapars, A.Science of Synthesis: Cross Coupling and Heck-Type Reactions, (20132228.

Palladium-catalyzed coupling of amides and aryl halides often provides complementary substrate scope to the corresponding copper-catalyzed method (Section 2.1.4.1.1). This may in part be due to differences in the reaction mechanism, a highly simplified version of which is shown in Scheme 21.[‌46‌‌48‌] The product 35 of oxidative addition of the aryl halide undergoes ligand exchange of halide X with the amide (“transmetalation”) in the presence of a base to form the complex 36. The “transmetalation” step can slow down if halide X is strongly bound to palladium, which is believed to contribute to the poor reactivity of aryl iodides with some of the palladium catalysts. It should be noted that this reactivity pattern is different from copper catalysis, in which aryl iodides are always more reactive than the corresponding aryl chlorides. The second problem in the “transmetalation” step manifests itself if the amide has poor binding affinity toward 35, as in hindered secondary amides. However, unlike copper catalysts, the palladium catalysts can be tuned to accept some of the less reactive secondary amides.[‌48‌] Finally, competitive formation of a κ2-complex 37 may also complicate palladium-catalyzed aryl amidations.[‌46‌,‌47‌]

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Mee eeeeeeeee-eeeeeeeee eeee eeeeeeeee eeeeeeee ee eeeee eeeeeeeee ee eee eeeeee ee eee eeeeee eee eeeeeeeee eeeeeeeeeeee ee eeeeee eee eeee eeeeeee eee eeeeee ee eee eeeeeee eeeeee (Meeeee 88). Meeeeeee (88) eeeeeeee eeeeeee eee eeee eeeeee eeee eeeeee eee eee eeeeeeee ee eeeeeeeeeeeeee ee eeeeeeeee eeee eeeeeeee eee eeeeeee eeee eeeeeee eeeeee eee eeeeeee.[‌88‌,‌88‌] Mee eeeeeeeeeee eeee eeeeeeeee, eeeeee eeeeeeeeeeeeee 88 (e-MeMeeeeMeee) ee 88 (Me8e-MeMMeee) eee eeeeeeeeeee.[‌88‌] Mee eeeeeeeee eeeeeeeee eeeeee, MeeeeeMeee (88) ee eeeeeeee eeeeee.[‌88‌] Meeeeee eeeee eeeeeee eeee eeee eeee ee eeeeeeeeeee eeeee, eee eeeeeee MMeee (88) ee eeeeeee eeeeee 88 (e-MeMMeee) eee eeeeeeeee ee eeeeeeeeee.[‌88‌,‌88‌] 8,8′-Mee(eeeeeeeeeeeeeeeee)-8,8′-eeeeeeeeee (88, MMMMM) eee 8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee (88, eeee) eeee eeee eeeeeeeeeeee eeeeeee eee eeeeeeeee ee eeeeeee eeeeeeeee eeee eee eeeeeee eeeeeee, eeee 8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee (88) eeeeee eee eeeeeeeee ee eee eeee.[‌88‌‌88‌]

Meeeee 88 Meeeeeeeeee Meeeeee eee Meeeeeeee-Meeeeeeee Meeeeeee ee Meeeee eee Meee Meeeeee

Mee eee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeeeeeee, ee ee eeeeeeeee ee eeeeeeee eee eeeeee eeeeeeeee(8) eeeeeeee. Meeeee eeeeeeeeee eeeeeee eeeee eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) ee (η8-eeeee)eeeeeeeeeeeeeee(MM) eeeee eeeeeee ee eeeeeeeee(MM) eeeeeee (eeeeeeee eee eee eeeeee eee eeeeeeeee eee eeeeeeeeee), eeeeee eeeeeeeee eeeeeee ee eeeeeeeeeeeee eeee ee eeeee ee eee-eeeeee eeeeeeeee(MM) ee eeeeeeeee(8), ee eeeee eeeeeeeeeeee eeeeeeee eeeeeeeee eeeeeeeeeeee.[‌8‌]

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

Meee eeeeee eeeeeeee eeeeeeeeee, eeeeee-eeeee eeeeeeee eeee Meeeeeee (88) ee eee eeeee eee ee eeeeeeee ee ee eeeeeeeee eeee eeeeeeee.[‌88‌] Meee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8) eeeeeee eeeeeeee e eeee eeeeeeee eeeeeeee eeee eeeeeeeee(MM) eeeeeee. Meeeee eeee-eeeeeeee ee eeee eee eeeeeee e eeeeee eeeeeeee ee eeee eeeee, eee eeeeeee eeeeeeeee eeeeeeeee eeeee (Me8MM8 ee ee eeee eeeee M8MM8) eee eeee eeeeeee ee eeeeee eeeeeee eeeeeeeee. Meee eee eeeeeeeee eeeeeeeee eeeee, eeeee eeeeeee ee eeeee eeee eeee eeeeeeeeee ee eeeeeeeeee eee eeeeeeee.[‌88‌] Meee ee eee eeeeeeee ee Meeeee 88 eee 8,8-eeeeeee ee eeeeeee eeeeeeee ee ee eeeeeeeeeee eeee eeee eeeee eeeeeee eee ee eeeeeeee eeee e eeee eeeeee eeeee eeeeeee eeee ee eeeeeee eeeee.[‌8‌] Mee eeeeeeee eeeeeeeeeeeee ee eeeee eeeeeeeee eee eeee eeeeeee eee eeeee eeeeeeee ee eeee eeeeee eeeeeeeeeeeeee eeeee 8 M.[‌88‌]

Meeeee 88 Meeeeeeee/Meeeeeee Meeeeeee eee Meeeeeeee ee Meee Meeeeee[‌88‌,‌88‌,‌88‌‌88‌]

Meeeeeeeeee 88

Me8 M M8 M8 Meeeeeeee Meeeeeeeeeeee (M) Meeeeeee (eee%) eee% ee 88 Meeeeeeeee Meeee (%) Mee
8-MeMM8M8 M M 8-MeMM8M8 8.8 Me8(eee)8 (8) 8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
M M MM8Me Me8(eee)8 (8) 8 Me8MM8, MMM, 88 °M 88 [‌88‌]
Me Me Me Me 8.88 Me8(eee)8 (8) 8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
Me M Me 8.88 Me8(eee)8 (8) 8 Me8MM8, eeeeeee, 88 °M 88 [‌88‌]
8-MeM8MM8M8 Me (MM8)8 8 Me(MMe)8 (8) 8.8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
Me Me (MM8)8 8 Me8(eee)8 (8.8) 8.8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
Me Me8(eee)8 (8) 8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
Me 8 Me8(eee)8 (8) 8.8 Me8MM8, eeeeeee, 888 °M 88e [‌88‌]
8-MeM8M8 Me Me8(eee)8 (8.8) 8.8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
8-MeM8MM8M8 Me Me MMe 8 Me(MMe)8 (8) 8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
8-MeM8M8 Me (MM8)8M 8.888 Me8(eee)8 (8) 8 M8MM8, eeeeeee, 888 °M 88 [‌88‌]
8-MMMM8M8 Me MM(Me)MM8M Me8(eee)8 (8.8) 8 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
Me (MM8)8 8.8 Me8(eee)8 (8) 88 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
Me 8.8 Me(MMe)8 (8) 88 Me8MM8, eeeeeee, 888 °M 88 [‌88‌]

e M eeeeee eeeeeeee [MeM (8 eee%), MMMMM (8; 88 eee%)] eeeeeeee 88% eeeee.

Meeeeeee (88) eeeeeeeeeeeee eeeeee ee eeee ee e eeeeee eee eeeeeeeee ee eeeeeeee-eeee eeee eeeeeeeee. Me eeeeeeee eeee eeeeeeeeee, eeeeeee eeeeeeeeeee eeeeeee eeee eeee eeeeeeeee, eeee ee 88 (Me8e-MeMMeee),[‌88‌] 88 (e-MeMeeeeMeee),[‌88‌] eee 88 (MeMe-MeeMeee).[‌88‌] Meeeee 88 eeeeeeeee eeeeeeee eeeeee eeeee-eeeeeeeeeeee eeee eeee eeeeee 88. Meeee eeeeeeeeeeee, eee eeeeeeee eeeeee eeeee eeeeee 88 ee eeeeeeeeee eeee eeee eeeeee eee M-eeeeeeeeeee eeeeeeeeee eeeeee ee eee eeee eeeeeeee. Mee eeeeeeee eee eeee ee eeeeeeeeeeee eeee eeee eeee eeeeeeee eee eeeeeeeeee. Mee eeee eeeeee eeeeeeee ee eeeeeeee eeeee eeeeeeeee(MM) eeeeeee eeee ee eeeeeeeeeeee ee eeeeeee eeee eee eeeeee eee e eeeeeeeee eeeeee ee eeeee, eeeee eeeeeeee eee eeeeeeeee ee eeeeeeeee(MM) eeee eee eeeeee ee eeeeeeeee eeeeee.[‌88‌] Me eeeee eeeeee eee ee eeee eeeeeeeeeeeee ee eeeeeeeee(MM) eeeeeee eeeeeeee e eeeeeeeee eeeeeeee ee eeeeeeeeeeeee eeee.[‌8‌] Meee eeeeeeee, eee eeeeee 88 eee eeee eeeeeeeee eeee e eeeeeeeee eeeee eeee eeeeeee eeeeee eeeeeeeee,[‌88‌] eeeeeeee eee eeeeeeeeeeee eee eeee ee eeeeee 88 eeeeeee eeeeeeeee ee eee eeee ee eeeeeee.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee Meee Meeeeeeee[‌88‌,‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 88

Me8 M8 M8 Meeeeeee (eee%) Meeeee (eee%) Meeeeeeeee Meeee (%) Mee
8-MMM8M8 M Me Me8(eee)8 (8) 88 (8) M8MM8, e-MeMM, 888 °M 88 [‌88‌]
8-MeMM8M8 M 8-MMM8M8 Me8(eee)8 (8) 88 (8) M8MM8, e-MeMM, 888 °M 88 [‌88‌]
8-MeMMM8M8 M Me Me8(eee)8 (8) 88 (8) M8MM8, e-MeMM, 888 °M 88 [‌88‌]
8-MeMMM8M8 M Me Me8(eee)8 (8) 88 (8) M8MM8, e-MeMM, 888 °M 88 [‌88‌]
8-Mee M MM8 Me8(eee)8 (8) 88 (8) M8MM8, e-MeMM, 8-Å eeeeeeeee eeeeee, 888 °M 88 [‌88‌]
8-eeeeeee M Me8(eee)8 (8) 88 (8) M8MM8, e-MeMM, 888 °M 88 [‌88‌]
M eeeeeeeeeee Me8(eee)8 (8) 88 (88) M8MM8, eeeeeee, 888 °M 88 [‌88‌]
8-MeM8M8 M 8-eeeeeee Me(MMe)8 (8) 88 (8.8) M8MM8, e-MeMM, 888 °M 88e [‌88‌]
8,8-Me8M8M8 M 8,8-Me8M8M8 Me(MMe)8 (8–8) 88 (8–88) Me8MM8, M8M (8–88 eee%), eeeeeee, 888–888 °M 88 [‌88‌]
8-MeMM8M8 Me(MMe)8 (8–8) 88 (8–88) Me8MM8, M8M (8–88 eee%), eeeeeee, 888–888 °M 88 [‌88‌]

e Meeeeeee eee eeeeeeeeeeee eeee 8 eee% M8M.

M eeeeeeeee eeeeee, MeeeeeMeee (88),[‌88‌] eee eeee eeeeeeeee eee eeeeeeeee ee eeeeeeeee eeeeee eeee eee eeee eeeeeeee eeee eeeee eeeeeeee ee Meeeee 88. Mee ee eee eeeeeeee ee eee eeeeeeee eeeeeeee-eeeeeeeeeee 8,8-eee(eeeeeeeeeeeeeee)eeeeee eeeeee, eeeeee 88 ee eeeeeeee ee eeeeeee e eeee eeeeeeeeeeeee eee eeee eeeeeeee eeeeeeee, eeeee eeeeeeeeeee eee eeeeeeeee “eeeeeeeeeeeeeee” eeee eeee eeeeeeee eeeee eeeeeeeeee (eee Meeeee 88). Meeeeee eeeeeeeeeee eeeeeee ee eee eeeeeeee ee e eeee ee eeeeeeeeee eeeee e eeeee ee eeee eeeeeeeeee [ee eee eeeee ee Me8MMM8M8 > Me8Me > Me8Me > Me8M; eeeee M8 = MM8, (MM8)8MM8], eeeeeeeeee eeeeeee eee eeeeeeee-eeeeeee eeeeee, eeee ee eeeeee, eeeeeeee eee eeeeeeeeeeeeeeee ee eee eeeeeeee. M eeeeeeeeee ee eee eeeeeeee ee eeee eeeeee eeeeeeee-eeee eeee eeeeeeeee ee eeeeeeeeee (e.e., eeeee eeeeeeeeee e 8-eeeeeee eeeee) eee eeee eeeeeeeeee. M eee eeeeeeeeeeeeee eeeeeeee eee eeeeeeeee ee Meeeee 88.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeee ee Meee Meeeeeeee eeee Meeeeeeee Meeeee Meeee eee MeeeeeMeee Meeeee[‌88‌]

Meeeeeeeeee 88

Me8 M8 M8 Meeee (%) Mee
8-MeMM8M8 Me Me 88 [‌88‌]
8,8-Me8M8M8 Me Me 88 [‌88‌]
8,8-Me8M8M8 Me Me 88 [‌88‌]

eeee-Meeee eeeeeeeee eeeeeeeeee ee eeeeeeeee eeeeeee eeeeeeeeee ee e eeeeeeeeeeee eeeeeeeee eeee. Meeeeee eeeeeeeee eeee eeee eeeeeeee eeeeeeeeeee eee eeeeeeeee-eeeeeeeee eeeeeeeee ee eeee-eeeee eeeeeeeee, eeeeeeeee eeeeeee eeeeeeeeeeeee eee-eeee-eeeeeeeeeeeeee/eeeeee eeeeeeeee,[‌88‌] MMeee (88)/eeeeee eeeeeeeee,[‌88‌] eee e-MeMMeee (88)/eeeeee eeee-eeeeeeee.[‌88‌] Me eeeee eeeeee/eeee eeeeeeeeeeee, MMeee (88)/eeeeee eeeeeeeee eeeeeeee eee eeee eeeeeeeeeeeee eeee eeee-eeeeeeeee eeeeee eeeeeee e-MeMMeee (88)/eeeeee eeee-eeeeeeee eeeeee eeeeeeee eeeeee eeeeeeeeee eeee eeeeeeee-eeee eeee eeeeeeee. Meeeeeeeeeeeee eeeeeeee, eeeeeeeee eeee-eeeee eeeeeeeeeeeeee 88, eee eeeee ee Meeeee 88. Me ee eeeeeeeeeee eeee eeee ee eee eeeee eeeeeee eeeeeeeee eeeee (e.e., 8888, 88) eee ee eeee eee eeee eeeeeeeeeeeeee ee eeee, eee eeeeeeeeeeeee e eeeeeeee eeeee ee eee eeeeeeeee ee eee eeee ee eeeeeee.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee eeee-Meeee Meeeeeeee[‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 88

Me8 M Meeeeeee (eee%) Meeeee (eee%) Meeeeeeeee Meeee (%) Mee
8-Mee Me Me(eee)8 (8.8) e-Me8M (8) MeMMe, eeeeeee, 888 °M 88 [‌88‌]
8-Mee Me Me(MMe)8 (8) 88 (8) Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
8-MeMM8M8 Me Me(eee)8 (8) e-Me8M (8) MeMMe, eeeeeee, 888 °M 88 [‌88‌]
8-MeMM8M8 Me Me8(eee)8 (8) 88 (8) e-MeMMe, eeeeeee, ee 88 [‌88‌]
8-MeMM8M8 Me Me(MMe)8 (8) 88 (88) Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
8-Me8MM8M8 Me Me8(eee)8 (8) 88 (88) e-MeMMe, eeeeeee, ee 88 [‌88‌]
8-M8MM8M8 Me Me(MMe)8 (8) 88 (8) Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
8-MeM8M8 Me Me(MMe)8 (8) 88 (8) Me8MM8, eeeeeee, 888 °M 88 [‌88‌]
Me Me(MMe)8 (8) 88 (8) Me8MM8, eeeeeee, 888 °M 88 [‌88‌]

Meeeeeeee eeee eee eeeeeee eeeeeeee eee eeeeeeeee eee eeeee ee eeeeeeee eeeee 8,8′-eee(eeeeeeeeeeeeeeeee)-8,8′-eeeeeeeeee (88) ee 8,8′-eee(eeeeeeeeeeeeeeeee)eeeeeeeee (88) eeeeeee. Meeeeeee eeeeeeee eee eeeee ee Meeeee 88.

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeee ee Meeeeeeee Meee ee Meeeeee Meeeeee Meeee 8,8′-Mee(eeeeeeeeeeeeeeeee)-8,8′-eeeeeeeeee ee 8,8′-Mee(eeeeeeeeeeeeeeeee)eeeeeeeee Meeeeee[‌88‌,‌88‌,‌88‌,‌88‌]

Meeeeeeeeee 88

Me8 M M8 M8 Meeeeeee (eee%) Meeeee (eee%) Meeeeeeeee Meeee (%) Mee
Me Me Me Me(MMMMM8)8 (8) 88 (8) Me8MM8, eeeeeee, 88 °M 88 [‌88‌]
Me M Me Me8(eee)8 (8.8) 88 (8.88) Me8MM8, e-MeMM, 888 °M 88 [‌88‌]
Me M Me8(eee)8 (8) 88 (8) Me8MM8, eeeeeee, 88 °M 88 [‌88‌]
Me M 8-eeeeeee Me8(eee)8 (8) 88 (88) Me8MM8, eeeeeee, 88 °M 88 [‌88‌]

Meeeeee ee eee eeeeee-eeeeeeeee eeeeeeeee, eee eeeeeeeeeeeeee eeeeeeeee-eeeeeeeee eeeeeeeee eee eeeeeee eeee eeeeee eeee eeeee eeeeeeeeeeeeee eeeeeeeeeeee. M eeeee eeeeeee ee eeeeeee eeee eeee eeee ee eeeeeeeeee eee eeeeeeeeeeeeee eeee eeeeeeeee, eeeeeeeee eee(8-eeeee)eeeeeeeee,[‌88‌] eee(8-eeeee)eeeeeeeee,[‌88‌,‌88‌] 8-(eeeeeeeeeeeeeeeee)-8′-eeeeeee-8,8′-eeeeeeeeee (MMM),[‌88‌] 8,8′-eee(eeeeeeeeeeeeeeeee)-8,8′-eeeeeeeeee (88),[‌88‌] Meeeeeee (88),[‌88‌] eee MMeee (88).[‌88‌,‌88‌] M eeeeee eeeee eee eeee eeeeeeeeeeee eeeeeeee eeeee eee(8-eeeee)eeeeeeeee (Meeeee 88).[‌88‌] Me eeeeeee ee eeeeeeeeeeeeee eeeeeeeee ee e eeeeeeee eeeeeeeee eeeee ee eeeeeeee ee Meeeee 88.[‌88‌] Me eeee eeee, MMeee (88) eeeeeeee eeeeeeeeeeeee eeeeee eeeee eeee eeeeee eee(8-eeeee)eeeeeeeee ee Meeeeeee (88).

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeee Meeeeeeee[‌88‌]

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeeeeeeeeee Meeeeeeee[‌88‌]

Mee eeeeeeee ee eeeeeeeee-eeeeeeeee eeee eeeeeeeee eee eeeee eeeeeee eeeee eee eeeeeeee eeeeeeeeee. Mee eeeeeee, e eeeeeee eeeeeee eee eeee eeee ee eeeeee eeeeeeeeeeeeeeee eee eeeeeeeeeeee, e.e. 88 (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeee-Meeeeeeee Meeeeee Meeeeeeee ee e Meeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

M-Meee Meeeee 88; Meeeeee Meeeeeeee:[‌88‌]

M eeeee-eeeee eeeeeeeeee Meeeeee eeee eee eeeeeee eeee Me(MMe)8 ee Me8(eee)8, Meeeeeee (88) [eeeee (Me/eeeeee) 8:8], eee eeeee eeeeeeee(e) [eee eeee eeeeee (8.8 eeeee), eee eee eeeee, eeeeeeeee, ee eeeeeeeeeee (8.8 eeeee)], eee Me8MM8 (8.8 eeeee). Mee Meeeeee eeee eee eeeeee eeee e eeeeee eeeeee, eeeeeeeee, eee eeeeeeeeee eeee eeeee (8 ×). Mee eeeeee eeeeeeee(e) eee eeeee 8,8-eeeeeee eeee eeee eeeee ee eeeeeee eeeeeee eee eeeeee. Mee eeeeee eee eeeeeeee eeee e Meeeee eeeee eee. Mee Meeeeee eeee eee eeeeee, eee eee eeeeeee eee eeeeeee ee eee eeeeeeeee eeeeeeeeeee (88–888 °M) eee 8–88 e, eeeee eee eeeeeeee eeee eeeeee eee eeee eeeeeeeeee eeeeeeee, ee eeeeee ee MM eeeeeeee. Mee eeeeeee eee eeee eeeeeee ee eeee ee ee, eeeeeee eeee MM8Me8 (88 eM), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee).

References


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