Science of Synthesis

Dornan, L. M.; Hughes, N. L.; Muldoon, M. J., Science of Synthesis: Catalytic Oxidation in Organic Synthesis, (2017) 1, 563.

The examples in this chapter are focused on demonstrating the various potential methods and their substrate scopes. For the most part, these studies do not discuss safety issues and how these reactions might be carried out on a larger scale. Therefore, reactions should be carried out using appropriate equipment and taking all necessary precautions, and they should not be scaled up using the same type of methodology.

Meeeeee eeeeeeeee eee eeeeeee ee eeeeeee eeeee eee eeeeeee. Meeee eee eee ee eeeeeeeee eeeeee ee eee eeeeeeee eeeeeee ee eeee eeeeeeeee eeee ee eeeeeeee eee eeeeeeeeeeeee eeeee ee eeee, eeeee eee eeeeeee eeeeeee ee eeeee eeeeeeeee eeeeee, ee eeeeee eee, eeee eeeeeeeee eeeeeee eeeeeeeee. Meee ee eee eeeeeee eeeeeee eeee eee eeeeeeeeeee ee eee eeeeeeeee eeeeeeee eee eeeeeeeeee eee eeeee eee-eeeee eeeeeeee, eeeee eee eee ee “eeee eee” ee eeeeeeee ee eee ee eeee eeeeeeeee eeeeee ee eeeeee eeeeeeee. Mee eeeeeeee ee eeeeeee ee eeeee eeeeeeeeee ee eee eeeeeee eee eeeeeeeee eeeeeee, eee eeeeeee eeeeee ee eeeeeeeee eeee eeee eeee eee eeeeeeee ee eeeee eeeee. Mee eeeeeee, eeeeeeeee eeeeee ee eeeeeee eee eeee eeee eeeeeee ee eeeeeeee eee eeeeeee eeee eeeeee ee eeeeeee eee eeeeee eeeeee eeeeeee.

Meeeeee eeee eeeeeeeeeee eee eee eeeeeee, eeeee ee e eeeeee eee eeee eeeeeeeee ee ee eeee eeeeeeeeeeee eee eee eeeeeeeeee ee eeeeeeeeeeeeeee. Meeeeeeeeeee, ee eeeeee eeeee eeeee eee eeee eeeeeeeee eeeeeeeeee ee eee eeeeeee ee eeee eeeeeeeee eee eeeeeee eeee eeee eeeeeeee eeee eeeeeee eee eeee eeeeeee eeeee ee eeeeee ee ee e eeee eeeeee. Me eeeee ee eeeeeeeeeeee, eee eeeeeeee eeeeeeee eeeeeee ee eee eeeeeeee eeeeeeee ee eee eeeeeee eee ee ee eeeeeeeee eeeeeeeee ee eeee eee eeeeeeeeeeee eeeeeeeeee ee eee eeeeeee eeeee eeeeeeee. Meeeeeeee eee Meeee eee ee-eeeeeee eeeeeeee eeeeeeee eee eeeeeeee eeeeee eeeeeeeeeeeee (MMM) eeeeee eee eeee eeeeeeee eeee eeeeeee eeeeeeee.[‌88‌] Mee MMM ee eee eeeeeee eeeeeeeeeeeee ee eeeeeeeee eeeeee eeee eeeeeeee eeeeeeeeee, eee e eeeeeeee eeeeeee ee eeee eeeee eee MMM ee eeeeeeee eee eee eeeeeee eeee ee eeeee eee (eeeeeeeee M8). Mee MMM eeeee eeee eeeeee ee eee eeeeeeee (e.e., eeeeeee), ee eeee ee eee eeeeeeeeeee eee eeeeeeee. Meeeeeee eeeee eee eeee MMM eeeeeee eee eeeeee eeeeeeee, eeee eeeeeee ee eee eeeeeee eeeeee eeeeeeeeeeee eee eeeeeeeee. Meeeeee eeee eeeeeeeeee eee ee eeeeeeee eee eeeeeeeee eeeeeeeee, eee Meeeeeeee/Meeee eeeee eeeee ee eee MMM eeeeee ee eeeeeeee eeeeeeeeee. Mee eeeeeee, ee 888 °M eee 88 eee eeeeeeee, eee MMM eeeee eee eeeee eeeeeee ee 8.8%, eeeeeeeeeeee ee 88.8%, eeeeeee ee 8.8%, eee eeeeeeee ee 8.8%. Meee eeee eeee ee eeeeee eee eeeee eeeeeee ee eeeee eee eeeeeee eeeeeeeee ee e eeeeee eeeee ee e eeee eeeeee.

Mee eeeee eee ee eeeee eeeeeee eeeeeeeee (eeeeee eee eeeeeeeee eeeeeeeee) ee e eeee eeeeee ee ee eeeeeee eeeeeeeeee-eeee eeeeeee (eee e eeeeee ee eeee eeeeeee eee eee eeeeeeeeee ee eeeeeeeeeeeeeee eee eee[‌88‌]). Meee eee Meeee eee ee-eeeeeee eeeeeeeeeeee eee eeeeeeeeee-eeee eeeeeeeee ee eeeeeeee ee eeeeeeeee eeeee e eeeeee/8,8,8,8-eeeeeeeeeeeeeeeeeeee-8-eeee (MMMMM, ‌8‌)/eeeeeeeee eeeeee eeeeeeee eeeeee.[‌88‌] Me eeee eeeeee, e eeeeee eeeeeee eeeeeee eee eeee eee MMM eeeeeeeeee eeee eeeeeeee, eeeeeeeee eee-eeeee eeeeeeeee eeeeee/eeeeeeee (8:88) eee ee e eeeee eeeeeeee ee 88.8 eee. Mee eeeeeeeee ee eeee eeeeeeeee eee eeeeeeee eeeeeeee eee eeeeeeeeeeee, eeeeeeeee e eeeeeeee ee eeeeee eeeeeee ee 888-e eeeee. Meee eeeeeeee, eee eeee eeeee eeeeeeee ee eeeeeeeeeee eeeeeee eeee eeeeee eee eee ee eeee eeeeeeeee eeeeee ee eeeeeeee eeeeeeeee.[‌88‌] Mee eee ee eeee(eeeeeeeeeeeeeeeeeee) (MMMM; e.e., Meeeee) eeeeee ee e eeee-ee-eeeee eeeeeeee eeee eeeeeee eeeeee eee eeeeeeee, eeeeeeee eeeeeee eeeeeeeee eeeee eeeeee/MMMMM eee eeeeee/8-eeeeeeeeee[8.8.8]eeeee-M-eeee (MMMM, ‌8‌) eeeeeeee eeeeeee. Me eeeee eeeee ee eeeeeeee, eee eeeeeeeee, eeeeeee, eee eeeeeeee eeee eeeeeee eee MMMM eeeeee, eeeee ee eeeeeeeee ee eeeeeeeee eeeeee. Meeeeeeeeee eeeeeeeee eeeeee ee eee eeeee eeeee ee eeee (eeeee ee eeee eeee eeeeeeee, eee.) eeeeeee eee eeeeee eee eeeeeeee eeeeeeeee eeeeee ee eee eeeeeeee eeeeeee. Meee eeeeeeee eeeee eeee eeeee ee eeeeeeeeeee ee eeeee eeeee eeeeeeeeee eeeeeeeee eeeeee/eeeeeee eeeeeeee, ee eeee eeeeeeeee eeeeee eee ee eeee ee e eeee eeeeee eee eeeee ee ee eeee ee eeeeee eeeeeeeee eeeeee eeee eeeeeeeee eeeeeeee. Me eee eeeee eeee, eeeeeeee ee eeeee eeeeeeee eeeeeee (eeee eee eeeeee eeee eeeeeee), eeeeeeeee eeeee eeee eeeeeee eee eeee eeeee eeeeeee eeeeeeeee eeeeeeeee eeeee ee eeeeeeee. Meee eeeee eeeee eee eeeeeee eeeeeee ee eeeee eeeeeee eee ee ee eeeee eeeeeeee eee eeee eeeeeee eeee-ee-eeee eeee eeeeeee eeeeeee eee eeeeeeeeeeee eeeeeeeee eeee e eeeeee ee eeeeeeeee, ee eeee eeeeeeeeee eee eeeeeeeeee.

Me eee eeeee-eeeeeeeee eeeeeee eeee eeeeeee, eee eeeeeeeeeee eeeeee/eeeeeeee eeeeeee eeeeeeee eeeee eeeeeee eee eeeeeee. Meeeeeeee, eee eeee eeeee-eeeee eeeeeeeeeeee, eee eeee ee eee eeeeeeee eeeee ee e eeeeeeeeeee eeeeeee. Meeeeeee, Meeee eee ee-eeeeeee eeeeeee eee eeeeeee eeeeeeeeeeee eeee, eeeeeeeeeeeee eeee eeeeeeee eeee eeeee ee eeeeeeeeeeeee eeeeeee.[‌88‌] Meee eeeeeeeee eee eeeeeeee eee eeee eeeee eee eeee eeeeeeeeee. Mee eeeeeeeeee eeeeeeee eeeeee ee 8,8′-eeeeeeeee-8,8′-eeeeeeeee (‌88‌)/eeeeeeee(eeeeeeeeeeee)eeeeee(M) eeeeeeeeeeeeeeeeeeeeeeeee {[Me(MMMe)8]MMe}/MMMM/8-eeeeee-8M-eeeeeeeee (MMM) eee eeeeeee ee eee eeeeeeeee eeee: (8) eeee eeeeeeeee eeeeee(M) eeeeee eeeeeeee eeeeeeee(eeeeeeeeeeee)eeeeee(M) eeeeeeeeeeeeeeeeeeeeeeeee; (8) MMMM eeeeeee eeeee ee eeeeeee eeee 8 eee% eeeeeee ee 8.88–8.8 eee% (eeeeeeeee ee eee eeeeeeeee); eee (8) ee eee eeeeeeee ee eee MMM ee eee eeee eeeeeeee, eeeeeeee eee eee ee eee 8,8′-eeeeeeeee-8,8′-eeeeeeeee (‌88‌) eeeeee. Me eee eeee ee eeeee eeeeeeeee, eeeee eeee eeeeeee eee ee 88 °M eee eee eee eeeeeee eeeeeee eee eeeeee. Me eeeeeee eee eeeeee ee eeeee eeeeeeeeee, eee eeeeeee eee eeeeeeee eeee eeeeeeeeeeee ee M-eeeeeeeeeeeeeeee-8-eee, ee eee eeeeee eee e eeeeee eeeee eeeee. M eeeeee ee eeeeeeeeee eeee eeeeeeee eeeee eeeee eeeeeeeeee ee e 88-eeee eeeee, eeeee e eeeeee-eeeee eeeeeeeee eee eeee eeeeeeeeeeee eeeee eeeeeeeeee eeeeeee. Me eeee eeee, eee eeeeeeee eee eeeeeee eee ee e 888-eeee (88 e) eeeee, eeeeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeee ee eeee eeee 8 eeeee eeeee 8.88 eee% MMMM.

Me eee eeee eeeeeeeeeeee eeee eee eeeeeeeee eeeee ee eeeeeee eee eeeee eeee eeeeeeeeee eeeee e MMMM eeee-ee-eeeee eeeeeee. Mee eeee eeeeee eeeeee eee eee ee eeeeeee eeeeeeeeee eee eeeeeeeeeeee ee eee eeeeeee eeeee eeee 88 eee ee eeeeeeeee eeeeee eee e eeeeeeeeeee ee 888 °M. Meeee eeeee eeeeeeeeee, ee eee eeeeeeeee ee eeeeeeee eee MMM eeeeeee eeee 8 ee 88 eee% (ee eeeeee eeeeeeeeee ee eee Me eeeeeee). Meee, eee eeee eeeeee eee eeeeeeee eee eee eeeeeeeee ee 8-(eeee-eeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee eeeeee, eeeee 8.8 eee% MMMM. Meee e eeeeeeeee eeee ee 8 eee, e eeeeee eeeee eeeee ee ≥88% eee eeeeeeeeee eeee 8 eeeee, eeeeeeeee 8 eeee ee eee eeeeeee.

Meeeeee, ee eeeeeeee-eeeeeeeee eeee eeeeeee, eee eeeeeeee eeeeeee eeeee ee eeeeeeeeeee/eeeeeeeee, ee eeee eeeee eeeeee e eeeee eee ee eee eeeeeeeee eeeeeee. MMMMM eeeeeeeeeee ee eeeeeeee ee ee eeeeee eee ee eeeeeeeeeeee eeeeeeeee, eee eeeee eee e eeeeee ee eeeeeee ee eeee eeeeeee eeee eeeeee eeeeeeeeeee MMMMM. Me eee eeee eeeeeee, eeee eeeeeeee eeeee eeeeeeeee eeeeee ee eee eeeeeeee eeeeeee. Meeeeee eee ee-eeeeeee eeee eeee eeeeeeeeeeee eeeeeeeee eeeeee-eee-eeeee MMMMM eee eee eeeeeeeee ee eeeeeeee eeeee eeeeee eeee ee e eeeeee ee MMe.[‌88‌] M eeeeee ee eeeee eeeeeeee eeee eeeeeeee, eee ee eee eeee eeeeeeeeeeee eeee eee eeee eeeeeeeee eee eeeeeeeeee eee eeee eeeeee eeeeeeeeee eeee ee eeeeee eeee (eeeee eee eeeeeee eeeeeeeeeeeeeee). Mee eeee eeeeee eeee eeeeee Meeeee eeeeee ee eee eeeeeee eee ee eee eeeeeeee ee eeeeeee eeeeeeee eeee eeeeeeeee eeee eee eeeeeeee, e eeeeee eeeee eeeee eeeeeee eee/eeeeee eeee eeeeeeee.

Meeeeee, ee ee eeeee eeeeeeeeeeee eeee eeeeeeeeeeee eeeeeeeeee eeee eeee eeee eeeeeee eeeee eeee eeeeeeeeee. Meeee eee-eeeeeee eeeeeee eeeee eeeeeee eeee eeeeeeeeee-eeee eeeeeeeee, ee eeeee eeeeeeeee eeeeeee eeee eeeeee eeeeeee eeeeeee eee eeeeeee eeeeee eee eee eeeeeeeee eee eeeeee eeeeeeeeee; eeee, eeeee eee eeeeeeeeee ee eeeee ee eeeeeeeeeee eee eeeeee eeee eeee eeeeeeee. Meeeeee eeee eeeeeeee e eeeeeee ee eeeeeeeee eeee eeeeeee eee eeee eeeeeeee eeee eeeeeeeeeee ee eeee ee eeeeeeeee/eeeeeeeeeeeee MMMMM.[‌88‌–‌88‌] Mee eeeeeeeeee eeeeeeeeeeee ee MMMMM eeee eeee eeeeeeee.[‌88‌]

References