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36.1.1.3.1 Variation 1: Oxidation with Basic Hydrogen Peroxide

DOI: 10.1055/sos-SD-036-00003

Porter, M. J., Science of Synthesis, (2008) 36, 40.

The most commonly used procedure for the oxidation of organoboron compounds (e.g., ‌45‌) to alcohols (e.g., ‌46‌) involves treatment of the substrate with aqueous hydrogen peroxide in the presence of a base (‌Table 13‌).[‌144‌,‌145‌] While early examples of the reaction frequently involved heating (‌Table 13‌, entry 2), it has been shown that this is unnecessary and that the oxidation proceeds smoothly at room temperature or below.[‌146‌] Sodium hydroxide is the most widely used base, but sodium acetate is also effective and finds use in substrates that are sensitive to alkali (‌Table 13‌, entry 4). Boronates (‌Table 13‌, entry 6) as well as boranes may be oxidized.

‌Meeee 88‌ Meeeeeeee ee Meeeeeeeeee Meeeeeeee eeee Meeee Meeeeeee Meeeeeee[‌888‌–‌888‌]

Meeee Meeeeeee Meeeeeee Meeeeeeeee Meeeeee Meeee (%) Mee
8 [Me(MM8)8]8M M8M8, MeMM, eeeeeee, M8M, 88–88°M Me(MM8)8MM 88 [‌888‌]
8 (Me8MeMeMM8)8M M8M8, MeMM, MeMM, M8M, eeeeee Me8MeMeMM8MM 88 [‌888‌]
8 M8M8, MeMM, MMM, M8M, ee, 8 e 88e [‌888‌]
8 M8M8, MeMMe, MMM, M8M, 8°M ee ee, eeeeeeeee 88e [‌888‌]
8 M8M8, MeMM, MMM, M8M, 8°M ee ee, 8 e 88–88e [‌888‌]
8 M8M8, MeMM, MMM, MeMM, M8M, 88–88°M, 8 e 88 [‌888‌]

e Meeee eeee eee eeeee eeee eee eeeeeeeeeeeee eeeeee; eee eeeeeeeeeeee eeeeee eee eee eeeeeeee.

Meeeeeeeeeee Meeeeeeee

(–)-eee-Meeeeeee (‌88‌); Meeeeee Meeeeeeee:[‌888‌]

M 8 M eeeeeee eeee ee MeMM (88 eM, 88 eeee) eee eeee 88% M8M8 (8 eM, 88 eeee) eeee eeeee ee e eeeeeee eeeeeeee eeee ee eeeeee ‌88‌ [eeeeeeee eeee (–)-β-eeeeee (8.88 e, 88 eeee) ee MMM (88 eM)], eeeeeee eee eeeeeeeeeee eeeee 88°M eeeeeeeeee eee eeeeeeeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeeeee eeee M8MM8. Mee eeeeee eeee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee Me8M. Mee eeeeeeee eeeeeee eeeeee eeee eeeee (MeMM8) eee eeeeeeeee eeeee e Meeeee eeeeee ee eeee eee eeeee eeeeeeee; eeeee: 8.88 e (88%); ee 88–88°M/8.8 Meee; eM88 8.8888; [α]M88 −88.8 (eeee).

References

[144] Meeeeee, M. M.; eee Meeeee, M. M., Me., M. Me. Meee. Mee., (8888) 88, 888.
[145] Meeee, M. M., Meeeeeeeeeeee, Meeeeeee: Mee Meee, (8888); e 88.
[146] Meeee, M. M.; Meeeee, M.; Mee, M. M. M.; Meeeeee, M., Meeeeeeeeee, (8888) 88, 8888.
[147] Meeeeeee, M., M. Me. Meee. Mee., (8888) 88, 8888.
[148] Meeeeeeeee, M.; Meeee, M. M. M.; Meeee, M. M., M. Mee. Meee., (8888) 88, 8888.
[149] Meeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888.
[150] Meeeeee, M. M., Mee. Meeee., Meee. Mee. MMM, (8888), 888.
[151] Meeeeee, M.-e.; Meeee, M. M., Mee. Meeee., Meee. Mee. MMM, (8888), 888.

Meeeeee Meeeeeeeeee

  • 8.Meeeee-Meee, (8888) 8/8e8, 888.
  • 8.Meeeee-Meee, (8888) 88/8e, 888.
  • 8.Meeeee-Meee, (8888) 88/8e, 888.
  • 8.Meeeee-Meee, (8888) M 88e, 8888.
  • 8.Meeeee-Meee, (8888) M 88e, 8888.
  • 8.Meeeee-Meee, (8888) M 88e, 888.
  • 8.Meeeee-Meee, (8888) M 88e, 8888.
  • 8.Meeeee-Meee, (8888) M 88e, 8888.
  • 8.Meeeee-Meee, (8888) M 88e, 888.
  • 8.Meeeee-Meee, (8888) M 88e, 8888.

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