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20.4.1.1.2.2 Variation 2: Via Carboxylate Phosphorus Intermediates

DOI: 10.1055/sos-SD-020-00605

Keller, P. A.Science of Synthesis, (200720618.

The activation of carboxylic acids by their conversion into a mixed carboxylatephosphate anhydride enables the subsequent facile addition of a second carboxylic acid unit to yield the anhydride, e.g. 8. Phosphorus reagents used include compounds 5,[‌12‌] 6,[‌13‌] and 7[‌12‌,‌14‌] (Scheme 3) and are easily prepared.[‌15‌‌17‌] This mild, high-yielding procedure is widely applicable to aliphatic, aromatic, and heteroaromatic systems (Scheme 4).[‌12‌,‌13‌]

Meeeee 8 Meeeeeeeee Meeeeeee Meee eee eee Meeeeeeeee ee Meeeeeeeeeee[‌88‌‌88‌]

Meeeee 8 Meeeeeeeee eee Meeeeeeeeee Meeeeeeeeee Meeee[‌88‌,‌88‌]

Meeeeeeeeee 8

M8 Meeeeeeeee Meeee (%) ee (°M) ee ee (°M/Meee) Mee
MM8MMeee eeeeeee, 88eee 88 888888 [‌88‌]
Me MM8Me8, 88eee 88 8888 [‌88‌]
(MM8)8Me Me8M/MM8Me8, 88eee 88 888888/88 [‌88‌]
8-M8MM8M8 Me8M/MM8Me8, 88eee 88 888888 [‌88‌]
MM=MMe Me8M/MM8Me8, 88eee 88 888888 [‌88‌]
8-Mee Me8M/MM8Me8, 88eee 88 8888 [‌88‌]
8-eeeeeee Me8M/MMM, 88eee 88 888888 [‌88‌]
8-eeeeeeeeeeee-8-ee M-eeeeeeeeeeeeeee/MM8Me8, 888eee 88 888888 [‌88‌]

e Meeeeeee eeee eee eeeeee, M8,M8=MM=MM.

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeeee Meeeeeeee (8, M8=MM8MMeee); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee M-eeeeeeeeeeeeeeee (8.88e, 88eeee) eee Me8M (8.8eM, 88eeee) ee eeeeeee (88eM) eee eeeee eeeeee eeeeee(eeeeeeeeeee)eeeeeeeee 8 (8.88e, 8eeee) eee eee eeeeeeee eee eeeeeee ee ee eee 88eee. Mee eeeeeeeee eeeeeeeeee eee eeeeeeee, eee eee eeeee eeeee eee eeeeee eeee eeee M8M (88 eM) eee eeeee ee eeee eee eeeeeee; eeeee: 8.88e (88%); ee 888888°M.

References