Navigation

0 Hits

  • Previous / Next

You are using Science Of Synthesis as a Guest.
Please login or sign up for a free trial to access the full content.
21.1.4.2.1.4 Variation 4: Palladium-Catalyzed Aminocarbonylation with In Situ Generated Carbon Monoxide

DOI: 10.1055/sos-SD-021-00092

Cook, G. R.Science of Synthesis, (200521123.

Methods to avoid the necessity for compressed carbon monoxide gas have been investigated. Metal carbonyl complexes can liberate carbon monoxide in situ, and this has been exploited for the aminocarbonylation of aryl iodides.[‌31‌] In the presence of acetonitrile, hexacarbonylmolybdenum(0) liberates 3 equivalents of carbon monoxide (Scheme 18). When carried out with aryl iodides 44, amines, and a palladium catalyst, aminocar­bon­ylation takes place to afford amides 45 in good yield. The reaction can be performed on solid support by tethering the aryl iodide to a Wang resin (e.g., 46, which is amino­carbonylated to give 47). Substrates tethered to Rink resins suffer from lower yields. 2,2-Bis(di­phenylphosphino)-1,1-binaphthyl ligands are optimal for aryl bromides.

Meeeee 88 Meeeeeeeeeeeeeeeee eeee Meeeee Meeeeee Meeeeeeee Me Meee[‌88‌]

Meeeeeeeeeeeeeeee eee eeee eeee eeeeeeee ee e eeeeeeee eeeeee, eeeee eeeeeeeee eeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeee-eeeeeeee eeee.[‌88‌] 8,8-Mee(eeeeeeeeeeeeeeeee)eeeeeeeee ee eee eeee eeeeee eee eee eeeeeeee, eeeee eeeeeeee eeeeee (e.e., 88) eeee eee eeeeeeee ee eeeeee eee eeee eeeeeee (e.e., 88) (Meeeee 88). 8,8-Mee(eeeeeeeeeeeeeeeee)eeeeeee eee 8,8-eee(eeeeeeeeeeeeeeeee)-8,8-eeeeeeeeee eeeeeee eeeeee eeeee eeeeee, eee 8-eeeeeeeeeeeeee eeeee ee eeeeeeee. Me eeeee eeeee, eeeeee eeeeeeeee eeeeeee eeeeeee ee eeee­eeeee eeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeee Meeee Meeeeeeeeeeeeeeee ee e Meeeeeee Meeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeeeeeee 88 ee Meeeeeee-Meeee Meeeeeee; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeeeeeeeeeeeee ee eeeeee eeeee.

M eeee eeee eee eeeeeee eeee Me(MMe)8 (88ee, 8.88eeee), MMMMM (88ee, 8.88eeee), Me(MM)8 (888ee, 8.88eeee), eee Me8MM8 (888ee, 8.8eeee). Mee eeee eeee eee eeeeeeeee, eeeeeeeeee eeee eeeee, eee eeee eeeeeee (8.8eM), eee eeee eeeeee 88 (8.8eeee), eee eeeee (8.88eeee), eee MeMM (8eM) eeee eeeee. Mee eeee eee eeeeee eeee e Meeeee eeeee eee eee eee eeeeeee eee eeeeeee ee 88°M eee 8e. Mee eeeeeee eee eeeeee ee ee, eee eeee M8 (888ee, 8eeee) eee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8e eee eeeeeeee eeeeeee e Meeeee eee, eee eee eeeeeeee eee eeeeeee eeee MeMMe. Mee eeeeeee eeee eee eeeeee eeee eee. ee Me8MM8, M8M, eee eeeee, eeeee (Me8MM8), eee eeeeeeeeee ee eeeeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe) ee eeee 88.

8-Meeeeeeeeeeeeeeee 88 ee Meeee-Meeee Meeeeeee; Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeeeeeeeeeeeee ee eeeeee eeeee.

M eeee eeee eee eeeeeee eeee eeeee (888ee, 8.8eeee), Me(MMe)8 (88ee, 8.888eeee), ­MMMMM (88ee, 8.888eeee), Me(MM)8 (888ee, 8.8eeee), eee Me8MM8 (888ee, 8.8eeee). Mee eeee eeee eee eeeeeeeee eee eeeeeeeeee eeee eeeee, eee eeee eeeeeee (8eM), eee eeeee 88 (8.88eeee), eee MeMM (8eM) eeee eeeee. Mee eeee eee eeeeee eeee e Meeeee eeeee eee, eee eee eeeeeee eee eeeeeee ee 88°M eee 8e. Mee eeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee eeeeeee (8×8eM), MMM (8 × 8eM), MMM/M8M (8:8, 8 × 8eM), MMM (8×8eM), MMM (8 × 8eM), MM8Me8 (8 × 8eM), eee MeMM (8 × 8eM). Mee eeeee eee eeeee eeeee eeeeeee eeeeeeee ee 88°M. Mee eeeee eeeee eee eeeeeee eeee MMM/MM8Me8 (8:8, 8eM) ee ee eee 8e. Mee eeeee eee eeeeeee ee eeeeeeeeee eee eeeeee eeee MM8Me8. Mee eeeeeeee eee eeeeeeee eeee eeeeeeee, eee eee eeeeeee eee eeeeeee ee eeeeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee) ee eeee eeeee 88.

M-Meeeee-8-eeeeeeeeeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

M eeee eee eeeeeee eeee 8-eeeee-8-eeeeeeeeeeeee (88; 8.88eeee), MeMM8 (8eeee), Me(MMe)8 (8.888eeee), eeee (8.888eeee), eeeeeeeee (8.88eeee), e-MeMM (8.88eeee), eee MMM (8eM). Mee eeeeeee eee eeeeeee eeee M8, eee eee eee eee eeeeeeeee eeeeeeeeee. Mee eeeeee eee eeeeeee ee eeeeeeeee eeeeeeeeeee eee 8888eee. Mee eeee eee eeeeeeeeee eeeeee ee ee, eee eee eeeeeee eee eeeeeeeee eeee MeMMe. Mee eeeeeee eeeee eee eeeeee eeee M8M, eeeee, eeeee (M8MM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 88%.

References


Cookie-Einstellungen