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2.12.2.1.1 Iridium-Catalyzed Borylation

DOI: 10.1055/sos-SD-218-00219

Ros, A.; Fernández, R.; Lassaletta, J. M.Science of Synthesis: Catalytic Transformations via C—H Activation, (20152417.

It has been demonstrated that the direct borylation catalyzed by (cycloocta-1,5-diene)(methoxy)iridium(I) dimer [{Ir(OMe)(cod)}2]/4,4′-di-tert-butyl-2,2′-bipyridyl (dtbpy) (1:2) system takes place through an [Ir(dtbpy)(BPin)3] (BPin = 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) intermediate, which does not have a vacant site to facilitate the coordination of the directing groups and the subsequent cleavage of an ortho-C—H bond. Different strategies based on the modification of the ligands and/or substrates have been developed to enable directing-group effects. The catalytic system formed by combination of (cycloocta-1,5-diene)(methoxy)iridium(I) dimer as the precatalyst and an electron-poor phosphine such as tris[3,5-bis(trifluoromethyl)phenyl]phosphine as the ligand promotes the borylation of benzoates 34 in a highly ortho-regioselective manner.[‌26‌] The reactions take place in octane at 80 °C over 16 hours to afford the corresponding products 35 in high yields and with complete regioselectivity, although an excess of arene (5 equiv) is required to avoid ortho,ortho′-diborylation byproducts. Methyl, ethyl, isopropyl, and tert-butyl esters are suitable directing groups, and the method tolerates substrates carrying electron-donating or electron-withdrawing functional groups (Scheme 9). The methodology can also be applied to the site-selective ortho-borylation of aryl ketones 36.[‌27‌] The substitution of the phosphine ligand by triphenylarsine increases the catalyst activity to enable the isolation of the products 37 in >100% yields, meaning that the generated pinacolborane can also act as boron source when all the limiting reagent, bis(pinacolato)diboron, is consumed (Scheme 9).

Meeeee 8 eeeee-Meeeeeeee Meeeeeeeee ee Meeeeeeee eee Meee Meeeeee[‌88‌,‌88‌]

Meeeeeeeeee 8

M8 M8 M8 M8 Meeeee (%) Mee
M M M Me 88 [‌88‌]
M M M eMe 88 [‌88‌]
Me M M Me 88 [‌88‌]
MMe8 M M Me 88 [‌88‌]
M MM8 M Me 88 [‌88‌]
M Me M Me 88 [‌88‌]
M M MMe8 Me 88 [‌88‌]

e MM eeeeee eeeee ee eee(eeeeeeeeee)eeeeeee.

Meeeeeeeeee 8M

M8 M8 M8 M8 Meeeee (%) Mee
M M M Me 888 [‌88‌]
M M M e-Me 888 (88) [‌88‌]
M M Me Me 888 [‌88‌]
M M Me Me 888 [‌88‌]
M Me M Me  88 [‌88‌]
MMe M M Me 888 [‌88‌]

e MM eeeeee eeeee ee eee(eeeeeeeeee)eeeeeee; eeeeeeee eeeeee ee eeeeeeeeeee.

Meeee-eeeeeeeee eeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeee eeeeeee eeeeeeee 88 eeeeeeeee eee eeeeeeee eeeee-eeeeeeeeee ee eeeeeeeeeeeeee eeeeee ee e eeee eeeeeeeee eeeeee.[‌88‌] Mee eeeeeeee eeeee eee eeeeee eeee eeeeeee eeeeeeeeee eeeeeeeee eeeeee, eeee ee eeeeeeeee, eeeeeeeeee, eeeeeeeeeeeeeee, eeeeeee, eee (eeeeeeeeeeeee)eeeeee, eee eeee eeee eeee eeeeeeeee, eeeeee eee eeeeeeeeeeeee eeeee-eeeeeeeee eeeeeeee 88 eeee eeeeeeee eeeeeeeeeeeeeeee eee eeee ee eeeeeeeee eeeeee ee eeee eeeee (Meeeee 88). Meeeeeeeeeeeee ee eee eeeeeeeee eeeeee ee eeeeeee, ee eee eeeeeeee eeeee eee eeeeeeeeeee eeeeee eeeeee ee (eeeeeeeee-8,8-eeeee)(eeeeeee)eeeeeee(M) eeeee eee eeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeee 88 (Me8 = Me; 8.8 eee% Me, 8:8 ee 8:8 [Me]/M eeeeee) eeeeeee eeee eeeee eeeeeeeeee ee 88 °M. Me eeeeeeee eeeee eeeee eeee eeeee eeeeeeeeee eeee ee 88 (Me8 = 8-M8MM8M8) ee eeeeeeeee-, eee-eeee-eeeee-, eeeeeeeeeeeee-, ee eeeeeeeeeeeeeeeeee eeeee eeeeeeeeeee eee eeee eeeeeeeeee. Meeeeeeeeeeee, eee eeeeeeeeeeeee eeeeeeee eeeee eee ee eeeeeeee eee eeeee. Meee eeeeeeeeeee eee eeee ee eeeeeee ee eeeeee eeeeeeeeeee eeee ee eeeeeeeeee, eeeeeeeeee, eeeeeeeeee eeeeeeee, eee eeeeeeeeee 88,[‌88‌] eee eeeeee eeeeeeee-8-eeeeeeeeeeee 88 (Meeeee 88).[‌88‌] Meeeeeeeee eeeeeeeee eeee eeeee eeee eeeeeeee eeeeeeeeeeeeeeee eee eeeeee eeeeeeeeeee, eee eeee eeeeeeee ee eeee eeeeee eee eeeeeeee eeee eeeeeeeeee.

Meeeee 88 eeeee-Meeeeeeee Meeeeeeeee ee Meeeeeeeeeeeee Meeeee eee Meeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

MM M8 M8 M8 M8 Meeeee (%) Mee
MM8Me M M M M 888 (88) [‌88‌]
MM8Me M Me M Me 888 (88) [‌88‌]
MM8Me Me M M Me  88 (88) [‌88‌]
MM8Me M eMe M M  88 (88) [‌88‌]
MM8Me MMe M M M 888 (88) [‌88‌]
MM8Me MM8 M M M 888 (888) [‌88‌]
MM8Me MMe M M Me  88e (88) [‌88‌]
MM8e-Me M M M M 888 (88) [‌88‌]
MMMMe8 M M M M  88 (88) [‌88‌]
MM8Me M M M M 888 (88) [‌88‌]
MM8MMMM M M M M  88 (88) [‌88‌]
8,8-eeeeeeee-8-ee M M M M 888 (888) [‌88‌]

e 8M MMM eeeeee eeeee ee eee(eeeeeeeeee)eeeeeee; eeeeeeee eeeeee ee eeeeeeeeeee.

e Meeee [eeeee/(eeee + eeee)] 88:8.

Meeeeeeeeee 88M

MM M8 M8 M8 M8 Meeeee (%) Mee
MMe M M M M 88e [‌88‌]
MMMM M M M M 88e [‌88‌]
MMM8Me M M M M  8 [‌88‌]
MMM8e-Me M M M M 88 [‌88‌]
MMM8Me M M M M 88 [‌88‌]
MMMMMe8 M M M M 88 (88) [‌88‌]
MMMMMe8 Me M M M 88 (88) [‌88‌]
MMMMMe8 M Me M M 88 (88) [‌88‌]
MMMMMe8 M Me M M 88 (88) [‌88‌]
MMMMMe8 M M MMe M 88 (88) [‌88‌]
MMMMMe8 M M Me M 88 (88) [‌88‌]
MMMMMe8 M Me M M 88 (88) [‌88‌]
MMMMMe8 M MM8MM8Me M M 88 (88) [‌88‌]

e 8M MMM eeeeee eeeee ee eeeeeeeeeeeee; eeeeeeee eeeeee ee eeeeeeeeeee.

e Meeee [eeeee/(eeee + eeee)] 88:88.

e Meeee [eeeee/(eeee + eeee)] 88:88.

Meeeeeeeeee 88M

M M8 M8 Meeeeee Meeeee (%) Mee
M M M eeeeee 88 (88) [‌88‌]
MMMMM M M eeeeee 88e [‌88‌]
M M Me e-eeeeee 88 (88) [‌88‌]
M Me M eeeeee 88 (88) [‌88‌]

e 8M MMM eeeeee eeeee ee eee(eeeeeeeeee)eeeeeee; eeeeeeee eeeeee ee eeeeeeeeeee.

e Meeeeeee eeeee.

M eeeeeeeee eeeeeeee eeeee eee ee eeeeeeeee eeeeee ee eeeeeeeeeee ee (eeeeeeeee-8,8-eeeee)(eeeeeee)eeeeeee(M) eeeee eee 8-eeeeeee eeeeeeeeee (e.e., 88) ee eee eeeeee. Me eeeee eeeeeeeeee M,M-eeeeeee, eee ee eee eeeeeeeee eeeeeeee eeeee ee e eeeeee eeeee eee ee eeeee ee eeeeeeeeeeee eee eeeeeeeee eeee ee eeeeeeee e eeeeeeeeeeee eeee eeeee eeeeeee ee eee eeeeeeeee. Meeee eeeeeeeee eee eeeeeeeee eee eee eeeeeeee-eeeeeeee eeeeeee-eeeeeeeee eeeee-M—M eeeeeeeeee ee 8-eeeeeeeeeeeee eee eeeeeeeeeeeee. Meeeeeeee ee eee eeeeee eeeeeeeeee ee eeeeeeeeeee, eee eeeeeeeee eeeeeeee 88 eeeeeee/ee eee eeeeeee eeeeeeee M—M eeeeeeeeeee ee eeee eeeeeeeee ee eeeeeeeee 88 (Meeeee 88).[‌88‌]

Meeeee 88 eeeee-Meeeeeeee Meeeeeeeee ee 8-Meeeeeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 M8 Meee (°M) Meeeee (%) Mee
(MM=MM)8 (MM=MM)8 M 88 88 [‌88‌]
(MM=MM)8 (MM=MM)8 Me 88 88 [‌88‌]
M Me (MM=MM)8 M 88 88 [‌88‌]
M Me (MM=MM)8 M 88 88 [‌88‌]
M MMe (MM=MM)8 M 88 88 [‌88‌]
(MM=MM)8 MMe M M 88 88 [‌88‌]
M M M M M 88 88e [‌88‌]
M M (MM=MM)8 M 88 88e [‌88‌]
Me M (MM=MM)8 M 88 88e [‌88‌]

e Meeeeeee eeeee eeeee eeeeee eeeeeeeeeeeeee.

e Mee Meeee eeee/eeee eeeeee 88 eeee eeeeeeee M—M eeeeeeeeeee eee eeeeeeee.

Meeeeeee M,M-eeeeeeeeeeeeeeeeee 88 eeeeeee eeeee-M—M eeeeeeeeee eeee eeeee eeeeeeeee ee eeee eeeeeeee 88 (Meeeee 88),[‌88‌] eee eeeeeeee M,M-eeeeeeeeeeeeeeeeee 88 eee ee eeee eee eee eeeee,eeeee′ eeeeeeeeeeee,[‌88‌] eeeeeeee eeeeee eeeeeeeee eeeeeeeeeeeee 88 eeeee eee ee eeeeeeeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeeee ee eee eeeeeeeee eeeeeeeeeeeee (Meeeee 88).[‌88‌] Meee eeeeee eeeeeeeee eeeeeeeeeeeee eeeeeeee-eeeeeeee eeeeee (MMe8, e-Me) ee eee 8-eeeeeeee ee eee eeeeeeee eeee eee eeeeeeee ee eeeee eee eeeeeeeeeee eeee eee eeee eeeeeeeee eee eeee eeee-eeeeeeee eeeee eeeeee eeeeeeeeeeeee (Meeeee 88).[‌88‌] Meeee eee 8-(eeeeeeeeeeeee)-eeeeeeeeeee eeeeee 88, eeeeeeee-eeeeeeee M—M eeeeeeeeee eeeee eeeee eeee eeeeeeee eeeeeeeeeeeeeeee eee eee eeeee eeeeeeeeee eeeeeeee eee ee eeee ee Meeeee–Meeeeee eeeeeeeee, eeeeeee eee eeeeeee eeeeeeeeeeee, ee eeee eeeeeeeeeeeeee eeeeeeee eeeeeeeeeee 88 eeee eeee eeee eeeeeeeeeee eeee eeeeeeee eeeeeeeeeeeee eee eee eeeeeeeee ee eeeeeeee eeeeee-eeee eeeee.

Meeeee 88 eeeee-Meeeeeeee Meeeeeeeee eee Meeeeeeeeeee ee M,M-Meeeeeeeeeeeeeeeee[‌88‌‌88‌]

Meeeeeeeeee 88

M8 M8 M8 Meeeee (%) Mee
M M M 88 [‌88‌]
Me M M 88 [‌88‌]
MMe M M 88 [‌88‌]
M M M 88 [‌88‌]
(MM=MM)8 M 88 [‌88‌]
M Me M 88 [‌88‌]
M M MMe 88 [‌88‌]
M M M 88 [‌88‌]
M M Me 88 [‌88‌]

e Meeeeeee eeeeee eeeee eeeeeeeeeeeeee ee eeeeeee eeeeeee.

Meeeeeeeeee 88M

M8 M8 M8 Meeeee (%) Mee
M M M >88 (88) [‌88‌]
M MMe M >88 [‌88‌]
M M M >88 (88) [‌88‌]
M Me M >88 (88) [‌88‌]
MMe M MMe >88 (88) [‌88‌]
Me M Me >88 (88) [‌88‌]

e Meeeeeeee ee 8M MMM eeeeeeee ee eee eeeee eeeeeeee eeeeeeee; eeeeee ee eeeeeeeeeee eee eeeeee eeeee eeeeeeeee eeee eeeeee ee eeeeeeeeeeeeee ee eeeeeee eeeeeee.

Meeeeeeeeee 88M

M8 M8 Me8 Meeeee (%) Mee
M M 8-Mee 88 [‌88‌]
M M 8-MMMM8M8 88 [‌88‌]
M MMe 8-Mee 88 [‌88‌]
M MMe 8-MMMM8M8 88 [‌88‌]
M Me 8-Mee 88 [‌88‌]
Me M 8-Mee 88 [‌88‌]
Me M 8-Mee 88 [‌88‌]

e Meeeeeee eeeeee eeeee eeeeeeeeeeeeee ee eeeeeee eeeeeee.

Me e eeeeeee eee, eeeee-M—M eeeeeeeeee ee eeeeeeee eeeeee 88 ee eeeeee eeeeeeee 88 eee ee eeeeeeeee eeeee e eeeeeee ee (eeeeeeeee-8,8-eeeee)(eeeeeee)eeeeeee(M) eeeee eee eeeeeee-8-eeeeeeeeeeeee ee eeeeee ee e 8:8 eeeee (Meeeee 88).[‌88‌] Me eeee eeeee, e eeeee eeeeee ee eee eeeee,eeeee′-eeeeeeeeeee eeeeeee 88 eeeeee ee eeeeeee. M eeeeeee eeeeeeeeee eeeee M,M-eeeeeeee-8-(eeeeeee-8-ee)eeeeeeeeeee ee eee eeeeee eeeeeee eee eeeeeeeeeee ee e eeeeeeee eeee eeeeeeeee eeeeee, eeeeeeee eeeeeeeeee eee eeeeeeee eeee eee eeeeeeeeeeee ee eee eeeeee[‌88‌] ee eeeeeeeeeee eee eeeee eeeeeeeeeeeeeeee.

Meeeee 88 eeeee-Meeeeeeee Meeeeeeeee ee Meeeeeee Meeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeeeeeeeee (%) Meeeee (88/88) Mee
Me M M M 88 [‌88‌]
M M M M 88 [‌88‌]
Me M M M 88 [‌88‌]
M M Me M 88 >88:8 [‌88‌]
M M Me M 88 88:88 [‌88‌]
M M MM8Me M 88 88:8 [‌88‌]
M Me M Me 88 >88:8 [‌88‌]

e Meeeeeeee eeeeeeeee eeee eeeee/eee(eeeeeeeeee)eeeeeee eeeee ee 8.8:8; eeeeeeeeee eeeeeeeeee ee 8M MMM eeeeeeeeeeee.

e Meeeeeeeee ee 8M MMM eeeeeeeeeeee.

Mee eeeee-eeeeeeeee eeeeeeeeeeeee eeeeeee eeeeee 88, eeeeeee eeee (eeeeeeeee-8,8-eeeee)(eeeeeee)eeeeeee(M) eeeee eee eeeee-eeeeeeeee eeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeeeeee eeeeee 88, ee eeee e eeeeeeeee eeeeeeee eee eee eeeeeeee-eeeeeeee M8—M eeeeeeeeee ee eeeeeeeee eeeeeeeeeee 88.[‌88‌] Me ee eeeee eeeeeeeeee eeee eeeee eeeeeeeeee eee eeeeeeeeeeeeee eeeeeeeee ee eee M8 eeeeeeee ee eee eeeeeeeeee eeee ee eeeeeee–eeeeeeeeee-eeee eeeeeeee ee eeee.[‌88‌] Mee eeeeeeee eeeeeeee eeeeeeee eeeee eeee eeeeeeeeee (88–88 °M; 8 eee% ee eeeeeeee) ee eeeeee e eeeeeee ee eeeeeeeeeee M8-eeeeeeeee eeeeeeeeee 88 ee eeee ee eeeeeeeee eeeeee eee eeeeeeee eeeeeeeeeeeeeeee (Meeeee 88). Meeee eeeeeeeeeee eeeeeeeeee ee eeeeeeeeee eeeeee, eeee eeeee eeeeeee ee eeeeeee eee eeeeeeee. Mee eeeeeee ee eeee M8-eeeeeeeeee eeeeeeeeeee eee eeee eeeeeeeeeeee ee eee eeeeeeeee ee e MMM8 eeeeeeee eeeeeeeeee.

Meeeee 88 Meee-Meeeeeeee Meeeeeeeee ee Meeeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 M8 M8 Meeeee (%) Mee
Me M M M 88 (88) [‌88‌]
Me M M M 88 (88) [‌88‌]
(MM8)8MMe M M M 88 (88) [‌88‌]
Me Me M M 88 (88) [‌88‌]
Me M Me M 88 (88) [‌88‌]
Me M Me M 88 (88) [‌88‌]
Me M Me M 88 (88) [‌88‌]
Me M M Me 88 (88) [‌88‌]
Me M M MMe 88 (88) [‌88‌]

e 8M MMM eeeeee; eeeeee ee eee eeeeeeee eeeeeeee ee eeeeeeeeeee.

Meeeeeeeeeee Meeeeeeeee

Meeeee 8-(8,8,8,8-Meeeeeeeeee-8,8,8-eeeeeeeeeeee-8-ee)eeeeeeee (88, M8 = M8 = M8 = M; M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M eeeee eeeeeeeeee {Me(MMe)(eee)}8 (8.8 ee, 8.888 eeee), eeee[8,8-eee(eeeeeeeeeeeeeee)eeeeee]eeeeeeeee (88.8 ee, 8.888 eeee), eee eee(eeeeeeeeee)eeeeeee (888 ee, 8.8 eeee) eee eeeeeee eeee M8, eee eeee eeeeeee eeee eeeeee (8 eM) eee eeeeee eeeeeeee (88, M8 = M8 = M8 = M; M8 = Me; 88.8 ee, 8.8 eeee). Mee eeeeeee eee eeeeeee ee 88 °M eee 88 e; MM eeeee: 88%.

8-(8,8,8,8-Meeeeeeeeee-8,8,8-eeeeeeeeeeee-8-ee)eeeeee Meeeeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M; MM = MMMMMe8); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeee, eeeee-eeeeeeeee eeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeeeeee (88 ee, 8.8 µeee, 8.888 eeee M/e), eeeee eeeeeeee eeeeee (8.8 eM), eee {Me(MMe)(eee)}8 (8.8 ee, 8.88 µeee) ee eeeeee (8.8 eM) eeee eeeeee ee e 88-eM eeeee eeee eeeeeeeeee e eeeeeeee eeeeeee eee, eee eee eeeeeee eee eeeeeee eee 8 eee ee 88 °M ee eeee eeeeeeee 88. Meeeee eeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M8 = M; MM = MMMMMe8; 888.8 ee, 8.8 eeee) eee eeeeeeeeeeeee (88.8 ee, 8.8 eeee) eeee eeeee ee eee eeee, eeeee eee eeee eeeeee eeee e eeeee eee. Mee eeee eee eeeeeee eeee eee eeeeeeee. Meeee eee eeeeeeeee eeeeeee eee eeee eeeeeee ee 88 °M eee 88 e, eee eeeeeee eee eeeeeeee eeeeeee e eeeee eeeee eeeeeeee eeee e eeeeee eeeeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Me eeeeeeee eeeeeeee (8,8,8,8-eeeeeeeeeeeeeeeee) eee eeeee ee eee eeeeeee. Mee eeeee eeeeeeee eee eeeeeeee ee eee-eeeeeeeeee eeeeeeeeeeeeee (MMM); eeeee: 888.8 ee (88%).

8-[8-(8,8,8,8-Meeeeeeeeee-8,8,8-eeeeeeeeeeee-8-ee)eeeeeeeeeeee]eeeeeeeeeeee [88, M8,M8 = M8,M8 = (MM=MM)8; M8 = M]; Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeee eeeee eeee eee eeeeeeee ee eeeeeeeeee eeeeee 88 (88.8 ee, 8.888 eeee) eee {Me(MMe)(eee)}8 (88 ee, 8.888 eeee) ee eeeee MMM ee eeee e eeee eeee e eeeee eeeeee ee 88 eM. Meeeeeeeee eee 8 e eee eeee ee eeeeeeeeee eeeeeeeeeee. Mee eee-eeeee eeeee eeee eee eeee eeeee eeeee. M eeeee Meeeeee eeee eee eeeeeee eeee 8-(8-eeeeeeee)eeeeeeeeeeee (888 ee, 8.8 eeee) eee eee(eeeeeeeeee)eeeeeee (888 ee, 8.8 eeee). Mee eeeeeeee eeeee eeee (8 eM) eee eeeeeeeeeeeee (8.8 µM, 8 eee%) eeee eeeee eee eee eeeeeee eee eeeeeee ee 88 °M eeeee eeeeeeeeeee ee eee eeeeeeee eeeeeeee (MMM eeeeeeeeee). Mee eeeeeee eee eeeeee ee ee eee eeeeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeee 8:8) ee eeee eee eeeeeee ee e eeeee eeeeee eeeee; eeeee: 888 ee (88%).

8,8-Mee(8,8,8,8-eeeeeeeeeee-8,8,8-eeeeeeeeeeee-8-ee)eeeeeeeeeeee M,M-Meeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeeee eeeee eeee eee eeeeeeee ee eeeeeeeeee eeeeee 88 (88.8 ee, 8.888 eeee) eee {Me(MMe)(eee)}8 (88 ee, 8.888 eeee) ee eeeee MMM ee eeee e eeee eeee e eeeee eeeeee ee 88 eM. Meeeeeeeee eee 8 e eee eeee ee eeeeeeeeee eeeeeeeeeee. Mee eee-eeeee eeeee eeee eee eeee eeeee eeeee. M eeeee Meeeeee eeee eee eeeeeee eeee eeeeeeeeeeee M,M-eeeeeeeeeeeeeeeee (88, M8 = M8 = M8 = M; 88 ee, 8.8 eeee) eee eee(eeeeeeeeee)eeeeeee (888 ee, 8.8 eeee). Meeee eeeee eeeeeeeeee/eeeee eeeeee, eee eeeeeeee eeeee eeee (8 eM) eee eeeeeeeeeeeee (8.8 µM, 8 eee%) eeee eeeee eee eee eeeeeee eee eeeeeee ee 88 °M eeeee eeeeeeeeeee ee eee eeeeeeee eeeeeeee (MMM eeeeeeeeee). Mee eeeeeee eee eeeeee ee ee eee eeeeeeeeeeee ee eeeeeee. Mee eeeee eeeeeee, eeeeeee eeeeeeeeeeee MMM eeeee eeeeeeeeee e eeeeee eeeeeeeeeeeee, eee eeeeee eeee eeeeee ee eeee eee eeeeeeeeeeee eeee eeeeeee ee e eeeee eeeeee eeeee; eeeee: 888 ee (88%). Meeeeeee eee eeeeee ee ee 88 eeee ee eeeeeeeee eee eee eeeee eee eeeeeeeee ee 88% (8.88 e).

8-Meeeee-8-(8,8,8,8-eeeeeeeeeee-8,8,8-eeeeeeeeeeee-8-ee)eeeeeeeee (88, M8 = Me; M8 = M8 = M8 = M); Meeeeee Meeeeeeee:[‌88‌]

Me e eeeeeeee, eeeee-eeeeeeeee eeeeeee-eeeeeeeeeee eeeeeeeeeee eeeeeeeee eeeeee 88 (8.888 eeee/e, 88.8 ee, 8 µeee, 8 eee%), eee(eeeeeeeeee)eeeeeee (88.8 ee, 8.88 eeee), eee eeeee eeeeeeee e-MeMMe (8.8 eM) eeee eeeeee ee e 88-eM eeeee eeee eeeeeeeeee e eeeeeeee eeeeeee eee. M eeee ee {Me(MMe)(eee)}8 (8.8 ee, 8 µeee, 8 eee%) ee e-MeMMe (8 eM), eee 8-eeeeeeeeeeeeeee (88, M8 = Me; M8 = M8 = M8 = M; 88.8 ee, 8.8 eeee) eeee eeeee eeeeeeeeeeee. Mee eeee eee eeeeee eeee e eeeee eee eee eeeeeee eeee eee eeeeeeee. Mee eeeeeee eee eeeeeee ee 88 °M eee 88 e, eee eeeeeeee eeeeeee e eeeee eeeee eeeeeeee eeee e eeeeee eeee. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Me eeeeeeee eeeeeeee (8,8,8,8-eeeeeeeeeeeeeeeee) eee eeeee ee eee eeeeeee ee eeeeeeeee eee eeeee ee 8M MMM eeeeeeeeeeee (88%). Mee eeeee eeeeeeee eee eeeeeeee ee eeee-ee-eeee eeeeeeeeeeee (888 °M/8 Meee); eeeee: 88 ee (88%).

References