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You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content. Variation 6: Arylphosphinic Esters or Acids by Arylation of Hydrogenophosphinates

DOI: 10.1055/sos-SD-031-02233

Cristau, H.-J.; Virieux, D.Science of Synthesis, (2007311995.

One of the most interesting syntheses of arylphosphinates 89 or vinylphosphinates 90 involves palladium-catalyzed arylation or vinylation of the P(O)H bonds of alkyl- or aryl(hydrogeno)phosphinates or dihydrogenophosphinates (Scheme 66).

Meeeee 88 Meeeeeeee eee Meeeeeeeee Meeeeeeee ee Meeeeeeeeeeeeeeeeeeee[‌888‌,‌888‌‌888‌]

Mee eeeeee, eeeee ee eeeee ee e eeeeeee eeeeeeeeeee ee eeeeeeeeeeee,[‌888‌‌888‌] eee ee eeee ee eee eeeeeeeee ee eeeeeeeeeeeeeeee[‌888‌,‌888‌,‌888‌] ee eeeeeeeeeeeeeeeee,[‌888‌] ee eeee ee ee eee eeeeeeeeee ee eeeeeeeeeeeeeeeee ee eeeeeeeeeeeeeeee.[‌888‌] Meeeee 88 eeeee eee eeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(8)-eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeeee 88 eeee eeee eeeeeeee. Meeeeeeeeeeeee eeeeeeeeee[‌888‌] ee eeeeeeeeeee[‌888‌] eee eeee eeeeeeee.

Meeeee 88 Meeeeeeee ee Meee- ee Meeeeeeeeeeeeee Meeeee[‌888‌,‌888‌‌888‌]

Mee eeeeeee eeeeee eee eeee eeee eee eeeeeeeeeeeeee eeeeeeeee, eee eeeeeeeeeeeeee eeeeeeeee,[‌888‌,‌888‌] ee eeeeeeee, eeee eeeee eeeeee ee eeeeeee.[‌888‌] Meeeeeeeeee, eee eeeeeeee ee eeee eeeeeeeee, eee eee eeeeeeeee eeeee eee eeeee eeeeeee eeeeeeeeee eeeeee ee eee ee e eeeeeeeeeeee eeeee.[‌888‌,‌888‌,‌888‌,‌888‌] Mee eeeeeeeeeee eeeeeee eeeeee ee eeeeeeeeee ee eee eeeeeeee eeeeeeeeeeeeeeeeeeee eee eeee eeeee eeeeeeeeeeeeeee, eee eeeeeee, ee eeeee-eeeeeeeeeee eeee eeeee,[‌888‌,‌888‌] e eeeeeeeeeeeeee eeeee,[‌888‌] ee e eeeeeeeeeeeeeee eeeee.[‌888‌] Mee eeeeeeee eeeeeeeeeeeeeeeeeeee eee eeee eeee ee e eeeeeeeeeeee eeeeeeeee.[‌888‌]

Mee eeeeeeeee eeeeeeee ee eeeeeeeeee eeeeeeeeeeeeee, eeee MM eeee eeeeeeeee eeeeee eeeee eeeeeeeeeee ee eee eeeeeeee eeeeeeeee eeeeeeee ee eee eeeeeee ee eeeeee eeee ee eee eeeeeeeee eeeee.

Meeeeee eeeeeeeeeee eeeeeee ee eeee eeeeeeeeeeeeeee eeeeeeeee ee eee eeeeeeee eeeeeeeee ee eeeeeeeeeeeee ee eeeeeeeeee eeeeee eee eeeeeeeeeeeeee ee eee MM eeee eeee e MMe8 eeee (Meeeee 88).[‌888‌,‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeee ee eee Meeeeeeee ee Meeeeeeeeeeeeeeeeeeee[‌888‌,‌888‌]

M eeeeeeeee eee eee eeeeeeeee-eeeeeeeee eeeeeeeee ee e M(M)M eeee eee eeee eeeeeeee,[‌888‌] eee eeeeeeee eee eee eeeeeeeee ee eeeeeeeeeeeee ee eeeeeeeeee.

Mee eeeeeeeee(8) eeeeeeee eee ee eeeeeeeee ee eeee eeee eeeeeeeeeee(eeeeeeeeeeeeeeeeee)eeeeeeeee(MM), eeee(eeeeeeeeeeeeeeeeeeee)eeeeeeeeeee(8), ee eeeeeeeee(MM) eeeeeee:[‌888‌,‌888‌,‌888‌,‌888‌,‌888‌,‌888‌] eee eeeee eee eeee eeee eeeeee, eee eeeeeeeee(MM) eeeeeee ee eeee eeeeeeeee. Me eeee eeeee, eeeeeeeeeeeee eee ee eeeeeeee ee M-eeeeeeeeeeeeeeee,[‌888‌] 8,8-eeeeeeeeeeee[8.8.8]eeeeee,[‌888‌] ee 8-eeeeeeeeeeeee.[‌888‌,‌888‌]

Meeeee eeeeee ee eeeeeeeeeeeeeeeeee eeeee 88 ee eeeeeeeeeeeeeeee eeeee 88 eee eeee ee eeeeeeee eeee eeeeeeeee eeeeeeeeee eeee ee e eeeeeeeee-eeeeeeeee eeeeeeee (Meeeee 88).[‌888‌,‌888‌] Me eee eeeee eeee ee eee eeeeeeee, eeeeee eeeeeeeeeee ee eeeeee ee eeee. Meeeeeeee eeee- ee eeeeeeeeeee eeee eeeee eeeee eeeeeeee eeee eeee eeeeeee, eeeeeeeeee eee eeeeeeeeee eeeeeeeeeeee ee eee eeeeeeeee eeee eeeeee ee eee eeeeeeeeee. M eee-eee eeeeeeeee eeeeeee eeeeeeeeeeee eeeeeee eeeeee eeeeeee eee eeeeeeeeeee ee eee eeeeeeeeeeee eeeeee eeeeeeeeeee ee eeee ee eeeeeeeeee.[‌888‌]

Meeeee 88 Meee- ee Meeeeeeeeee ee Meeeeeeeee Meee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌,‌888‌]

M eeeeee eeeee-eeee eeee eee eeeeeee eeee ee eeee eeeeeee (8eeee), e eeeeeeeeeeeeeeeeeeee (8.8eeee), Me8M (8.8eM, 88eeee), eee Me(MMe8)8 (888ee, 8.8eeee). [Meee: Me eeeee eeeee eee eeee eeeeeee eee e eeeee, eeeeeee (8eM) eee eeeee ee e eeeeeee.] Mee eeee eee eeeeeee eeee M8, eeeeee, eee eeeeee ee ee eee eeee ee 88888°M eee 888e. Meee eee eeeeeee eee eeeeee, Me8M (88eM) ee MeMMe (88eM) eee eeeee, eee eee eeeee Me8MMMe eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeeeeeeeee ee e eeeeee eeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee [eeeeee eee, eeeeeeeee eeeee (ee 8888°M)/MeMMe]. Mee eeeeeeee eeeee ee eeeeeee eeeeeeee ee eeeeeeeeeeee ee eeeeeeeeeeeeeee.

Meeeee Meeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeeeeeeeee M8M(M)MM (88ee, 8.88eeee), eeeeeeee ee eeeeee eeeeeeeeeee ee 88% ee M8MM8, eee eeeeeee eeee MM(MMe)8 (888ee, 8.8eeee) ee e eeeeeeee-eeeeeeeeee eeeeee ee 88°M eeeee M8 eee 8e. Mee eeeeeeeee eeee eee eeeee ee e eeee ee ee eeeeeeeee (8.88eeee), M-eeeeeeeeeeeeeeee (88ee, 8.88eeee), Me(MMe)8 (8.8ee, 8.888eeee), eee Me8M (88.8ee, 8.88eeee) ee MeMM (8.8eM). Mee eeee eee eeeeeeee eeeee M8 eee 8e, eeeeee ee ee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeee eeee MeMMe, eee eeee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeeee eee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMM) ee eeeee e eeeeeeeee eee.

Meeeee Meeeeeeeeeeeeeeeee 88; Meeeeee Meeeeeeee:[‌888‌]

Meeee eeeeeeeeeee M8M(M)MM (8.8ee, 8.888eeee) eee eeeeeee eeee MM(MMe)8 (88ee, 8.888eeee) ee e eeeeeeee-eeeeeeeeee eeeeee ee 88°M eeeee M8 eee 8e. M 8-eM eeee eeeeeeeeee MeMM (888μM), eeeeeee eeeeeeeee eeee M8M88, eee eeeeeee eeee ee eeeeeeeee (888μeee), Me8M (8.8ee, 8.888eeee), Me(MMe)8 (8.8ee, 8.88eeee), eee Me8M (88ee, 8.8eeee). Mee eeee eee eeeeee eeeee M8, eee eeeeee eeeeeeeeeee eeee eee eeeee ee eeeeeee, eee eee eeeeeee eee eeeeee ee ee eee eeee ee 88°M eee 8e. Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe).