Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via
36.1.2.1.7.9 Variation 9: Using Single-Electron-Transfer Reduction Strategies

DOI: 10.1055/sos-SD-036-00032

Cox, L. R.Science of Synthesis, (200836108.

A wide range of reagents and reaction systems has been shown to reduce aldehydes (and ketones) to alkanols through single-electron-transfer mechanisms, although dimerization of the radical intermediate, to provide pinacol products, can be a particular problem for aldehyde substrates, and is often difficult to prevent. This section describes some of the more successful reduction methods in this class for aldehydes; for a more comprehensive discussion of these methods, the reader should refer to the section on ketone reduction, where these approaches are generally far more successful (see Section 36.1.2.2.1.9).

Meeeeeeee eeeeeee eeeeeeee eee eeeeeeeee ee eeeeeee eeee eeeeeeee (Meeee 88, eeeeeee 88),[‌888‌‌888‌] eeeeeeeee (eeeeeee 88),[‌888‌‌888‌] ee eeee (eeeeeee 888)[‌888‌,‌888‌,‌888‌‌888‌] eee eeee ee eeeeeeeeeee eeee ee eeeeeeee, eeeeeee e eeeeeeeeee eeeee eeee, ee eee eeeeeeee ee eeeee. Mee eeeeeee, eeeee eeeeeeee eeeeeeeee eeee eeee eeeeeeee eeee eeeeeeee eeeeee ee eeeeee eeeeeeeee ee eeeeeeee 88. Mee eeeeee ee eeeee eeeeeeee eeeeeeeeee eee eeeeeeeeeeeeeeee ee eee eeeeeeee; eeee eeeeee eeeee eeeeeeeee eeeeee eeeeeee eeeeeeee eeeeeeee eeeeeeeeeeeeee, eeeeeee eeeeeeeeee eeeee eeeeeeeee, ee eeeeeeeeee eeee(MM) eeeeeeee, eeeeeee eee eeeeeee eeeeeeeee eeeeeee ee eeeeeeeee eeeee (eeeee 8).[‌888‌] Me eeee eeeee eee eeeeeeeeeeeeee eeeeeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeeeee ee eeeeeeee.[‌888‌,‌888‌] Mee eeee eeee eeeeeee eeeeeeee eeeeeeee eee eeeee eee eeeeeeee ee eee ee eeeee eeeeeeeee eeeeeeee eeee eeeeeeeee eee eee ee eeeeeeeeee eee e eeeeee-eeeeeeee-eeeeeeee eeeeeee; eeeeee, ee eeee eeeee eee eeeeeeeee ee eeeeeeee eee eeeeeeeeee ee e eeeeeeeee eeeee eeeeeeee e eeeeeeee eeeeeeeeeeeee eeeeeee ee eeeeeeeee. Meee (eeeee 88)[‌888‌] eee eeee[‌888‌] eeee eeee eeee ee eeeeee eeeeeeeee eeeeeee eeeeeeeee eeee eeeeee eeee ee eeee ee eee (ee)eeeeeee.

Meeee 88 Meeee-Meeeeeee Meeeeeeee ee Meeeeeeee[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌‌888‌,‌888‌‌888‌]

Meeee M8 Meeeeeeeee Meeee (%) Mee
8 Me MeM8 (8 eeeee), Me eeeeee (8.8 eeeee), M8M eeeee [‌888‌]
8 Me Me (8 eeeee), MeMe8 (8.8 eeeee), MMM/M8M (8:8), ee, 88eee 88 [‌888‌]
8 (MM8)8Me Me (8 eeeee), MeMe8 (8.8 eeeee), MMM/M8M (8:8), ee, 8e 88 [‌888‌]
8 (MM8)8Me Me (8 eeeee), MeMe88M8M (8 eeeee), MMM/M8M, 8e 88 [‌888‌]
8 Me Me (8 eeeee), MeMe88M8M (8 eeeee), MMM/M8M, 8e 88 [‌888‌]
8 (MM8)88Me Me eeeeee (88 eeeee), MeMe8 (8 eeeee), M8M (888 eeeee), MMM, ee, 88eee 88 [‌888‌]
8 Me Me eeeeee (88 eeeee), MeMe8 (8 eeeee), M8M (888 eeeee), MMM, ee, 88eee 88 [‌888‌]
8 Me Me (8 eeeee), MeMe88M8M (8 eeeee), MeMM, eeeeee, 8e 88 [‌888‌]
8 (MM8)8Me Me (8 eeeee), MeMe88M8M (8 eeeee), MeMM, eeeeee, 8e 88 [‌888‌]
88 Me Me (88 eeeee), MeMe88M8M (8 eeeee), MMM/M8M (8:8), ee, 88eee 88 [‌888‌]
88 (MM8)88Me Me (88 eeeee), MeMe88M8M (8 eeeee), MMM/M8M (8:8), ee, 8e 88 [‌888‌]
88 Me Me, eeeeeee MeMM, ee, 88e 88e [‌888‌]
88 (MM8)8Me Me (8 eeeee), 8M MMe/MMM (8:8), 88°M, 8888e 88 [‌888‌]
88 (MM8)8Me Me, M8, MeMM, ee, 8eee 88 [‌888‌]
88 (MM8)8Me MeM8 (8 eeeee), MeMM (8 eeeee), MMM, ee, 8e 88e [‌888‌]

e Meeeeeee ee eee eeeeeee.

e Me MM.

Meeeeeee(MM) eeeeee, ee eee eeeeeeee ee eeeeeeee,[‌888‌] eee eeeeeeee eeeee eeeeee, ee eee eeeeeeee ee ee eeeeeeeee eeee ee 8M eeeeeeeeeeee eeee (Meeee 88, eeeee 88)[‌888‌] ee eeeeee (eeeeeee 88, 88),[‌888‌] eeee eeee eeee ee eeeeee eeeeeeeee eeeeeeeee ee eeee eeeee; eeeeeeee eeeeeeeee eee eeee eeeeeeeeee eee eeeee eeeeeeeeee eeeee ee eee eeeeeeeeeeee eeeeeeeee ee eeeeeee eeeeeeee eeeeeeee.

Meeeeeee ee eeeeeeee eeee ee eeeeeee eeeeeeee ee eeeeeeee(MMM) eeeeeeee eeeeeeeeee eeeee ee eee eeeeeee eeeeeee. Meeeeee, eeee eee eeeeeeee(MMM) eeeeeeee ee eeeee ee e eeeeeeee ee eee eeeeeeee ee eeeeeee, eeeeeeeee ee eee eeeeeee eeeeeee eeeeee eeeeeeeeeeeeee.[‌888‌,‌888‌] Mee eeeee ee eeee eeeeee ee eeeeeee ee eeee eeeeeeeee. Meeeeeeeee(MMM) eeeeeeee eeee eeee eeee eeeeeeeee, eeeeeeee ee eeee eeee eee eeeeeee eeeeeeee eeeeeeee eee eeeeeee­eeee eeee eeeeeeee.[‌888‌]

M eeeeeeeeeee ee eeeeeee eeeee, 8,8-ee-eeee-eeeeeeeeeeeee, eee e eeeeeeee eeeeeeeeee eeeee eeee, eeee ee eeeeee(MM) eeeeeeee eeeeeeeee,[‌888‌,‌888‌] eeeeee(MM) eeeeeeee eeeeeeeee,[‌888‌] ee eeee(MM) eeeeeeee eeeeeeeeeeee,[‌888‌] eeeeeeee e eeeeee eeeeeee eeeeee eee eeeeeeee eeeeeeeee ee eeeeeee eeeeeeee,[‌888‌] eeeeeeee eeeee eee eeeee eeeee ee ee eeeeeeeee (eeeeeeee eeee eeeeee eeeeeeee eee eeeeeee) ee eee eeeeeeeee ee eeeeeee eeeeeeeee eeeeeeeeeeee eeeeeeee.

Meeeeeee Meeeeeee eeeeeeee eee eeeeeeeeeeeee eeeeeeee eeeeeeeee eeeeee eeeeeeee eeeeee ee eeeeeeeeee ee eeeeeeeeee eeeee eeeeeeeeeeee eeeeeeee. Me eee eeee ee eeeeeeeee, eeeeeee, eee eeeeeeeee ee eeeeeee eeeeeeee eee eeeeee eee eeeee ee eee eeeeeee eeeeeee eeeeeee eeeeeee. Meeeeeee eee ee-eeeeeee eeee eeeeeeee Meeeeeee eee eeeeeeeeeeee eeeeeeee ee eee eeeeeeee ee e eeee eeeeeeeeee eeeeeeeee eeeeeeee Meeee eeee, eeeeeeeeeeeeee eee(8,8-ee-eeee-eeeee-8-eeeeeeeeeeeeeee), ee eeeeee eeeeeeeee ee eee eeeeeeee ee eeeeeee (Meeeee 88).[‌888‌] Meee eee ee-eeeeeee eeee eeeeeeeeeee(eeeeeeeeeeeeeeee)eeeeeeee(MM) ee ee eeeeeeee eeee Meeeeeee eeeeeeee ee eeeeeee eee eeeeeeeeeee eeeeee eeeeeeeee, eeeeeeee ee eee eeee ee eeeeeeeee eee eeeeeeeee eeeeeeeeeeee eeeeeeee ee eee Meeeeeee eeeeeee eee e eeeeeeeeeee eeee eeeeeeee.[‌888‌]

Meeeee 88 Meeeeeeeeeeeee Meeeeeeee ee ee Meeeeeee ee eee Meeeeeee ee e Meeeee Meeee eeee-Meeeeeeeeeee eee e Meeee Meeeeeee Meeee Meee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee Meeeeee (88, M8=Me; Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

MeMMM (888 μM, 8.8eeee) eee eeeee ee e eeeeeeeeee ee MeM8 (888ee, 8.8eeee) ee M8M (8eM). Me eeeeee (88ee, 8.8eeee) eee eeee eeeee ee eee eeeeeee. Mee eeeeeeee eee eeeeeee eee 88e eee eeee eeeeeeeee eeee Me8M. Mee eeeeeee eeeee eee eeeeeeeee eee eeeee (Me8MM8). Meeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eeeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee eeeeeeee eee eeeeeee; eeeee: 888ee (eeeee).

Meeeee Meeeeee (88, M8=Me; Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

M8M eee eeeee eeeeeeee ee e eeeeeee ee MeMe88M8M (888ee, 8.8eeee), Me (88ee, 8.8eeee), eee MeMMM (888 μM, 8.8eeee) ee MMM (8eM) ee ee. Me eeeeeeeeee eeeeeeee eee eeeeeeeeee ee M8 eeee eeeee. Meeee 8e, eee eeeeeeee eee eeeeeeee ee eeeeee 8% ee MMe. Mee eeeeeee eee eeeeeeeee eeee MM8Me8, eee eeeeeeee eeeeeee eeeeeeeee eeee eeeee (MeMM8), eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee eee ee eeeeee eeeeeeeeeeeeee; eeeee: 888ee (88%).

Meeee-8-ee [88, M8=(MM8)8Me; Meeee 88, Meeee 88]; Meeeeee Meeeeeeee:[‌888‌]

Me (888ee, 8.8eeee) (eeeeeee eeeeeee eeee eeeee) eee eeeee ee eeeeeee eeeeeeee eeee 8e ee e eeeeeeeeee ee eeeeeee (888 μM, 8.8eeee) ee 8M ee MMe/MMM (8:8; 8eM). Me eeeeee eee Me eeeee eee eeeeeee eeeeee eeeeee, eeeeeeee eee eeeee eee eeeeeeeeee eeeeeeeeeee. Meeeeeeee ee eeee eee M8(e) eeee eeee eeeeeee. Meeee 8888e ee ee, eee eeeeeee eee eeeeeeeeeee eee eeee eeeeeeeee eeee MeMMe/eeeeee (8:8). Mee eeeeeee eeeee eee eeeeee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee; eeeee: 888ee (88%).

References


Cookie-Einstellungen