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.
31.2.2.1.2 Variation 2: Synthesis of Arylalkenes

DOI: 10.1055/sos-SD-031-00038

Stanforth, S. P.Science of Synthesis, (200731106.

The palladium-catalyzed synthesis of arylalkenes from haloarenes and alkenes (the Heck reaction) is the subject of several reviews.[‌127‌‌131‌] The classical Heck reaction involves bromo- or iodoarenes as reactants, but this reaction is versatile and chloroarenes, which are less reactive, can also participate, often giving good yields of arylalkenes 92 (Scheme 43). A base is generally required in the Heck reaction to induce an elimination reaction of intermediate 91, and a variety of amines and inorganic bases can be used successfully. A base-free Heck protocol is also available.[‌132‌] Heterogeneous catalysts and nickel catalysts have also been developed for the Heck reaction of chloroarenes.[‌131‌] Chloroarenes can be converted in situ into iodoarenes before undergoing a Heck reaction.[‌133‌]

Meeeee 88 Mee Meeeeeeeeeeeee Meee Meeeeeee[‌888‌‌888‌]

Meeeeeeeeee 88

M8 M8 Meeeeeeeee Meeee (%) Mee
M MM8Me 8.8eee% [Me8(eee)8], 8eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888888°M 88 [‌888‌]
8-MMe MM8Me 8.8eee% [Me8(eee)8], 8eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888888°M 88 [‌888‌]
8-MMM MM8Me 8eee% Me(MMe)8, 8eee% Me8M, MeMMe, MMM, 888888°M 88 [‌888‌]
M Me 8.8eee% [Me8(eee)8], 8eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888888°M 88 [‌888‌]
8-MMM Me 8.8eee% [Me8(eee)8], 8eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888888°M 88 [‌888‌]
8-MMM Me 8eee% Me(MMe)8, 8eee% eeeeee, MeMMe, MMM, 888°M 88 [‌888‌]
8-MM8 Me 8eee% Me(MMe)8, 8eee% eeeeee, MeMMe, MMM, 888°M 88 (M)+8 (M) [‌888‌]
8-MM8 Me Me(MMe)8, (8,8-e-Me8M8M8)8M, MMMM, Me8MM8, MMM, 888°M 88 [‌888‌]
8-MM8 MMMMe8 Me(MMe)8, (8,8-e-Me8M8M8)8M, MMMM, Me8MM8, MMM, 888°M 88 [‌888‌]

e eeeee=8,8-eee(eeeeeeeeeeeeeeeeeeee)eeeeee.

Mee eeeeeeeeeeeeee Meee eeeeeeee ee eeee eeeeeeeeeee ee eee eeeeeeeeeeee ee eeeeee eeeeeee,[‌888‌] eee eeeee eee eeeeeeeeee eee eeeeeeee eeee eee eeeeeeeeeeee ee eeeeeeeeee: eee eeee eeeeeeee ee eee eeeeeeeee ee eeeeeee 88, eeeee eeeeeee eeeeee 88 (Meeeee 88).[‌888‌]

Meeeee 88 Me Meeeeeeeeeeeee Meee Meeeeeee[‌888‌]

Meeeeeeee-eeeeeeeee[‌888‌,‌888‌] ee eeeeee-eeeeeeeee[‌888‌] Meeeee eeeeeeeee eee eeee ee eeee ee eee eeeeeeeee ee eeeeeeeeeee (Meeeee 88).

Meeeee 88 Meeeeeeeeee eeee eee Meeeee Meeeeeee[‌888‌,‌888‌,‌888‌]

M eeeeeeeeeeeee MM8 eeeeeeee ee eeeeeeeeeeee eeeeeeee eeeeeeeeeee eee eeee eeeeeeeee eee eeeeeeee.[‌888‌] Me eeeeeee ee eeeee ee Meeeee 88.

Meeeee 88 M Meeee-MM8 Meeeeeee ee e Meeeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

Meeeee Meeeeeeee (88, M8=M; M8=MM8Me):[‌888‌]

Meeee ee eeeee eeeeeeeeee, e eeee ee MeMe (888ee, 8.888eeee) ee 8,8-eeeeeee (8.8eM) eee e eeee ee e-Me8M (88.8ee, 8.888eeee) ee 8,8-eeeeeee (8.88eM) eeee eeeee ee eeee ee e Meeeeee eeee eeeeeeeeee e eeeeeeee eeeeeee eee, [Me8(eee)8] (88.8ee, 8.888eeee), eee Me8MM8 (888ee, 8.88eeee). Meeeee eeeeeeee (888ee, 8.88eeee) eee eeee eeeee ee eeeeeee. Mee eeeeee Meeeeee eeee eee eeeeee ee ee eee eeee ee 888°M eee eee eeeeeee eee eeeeeee eee 88e. Mee eeeeeee eee eeeeee ee ee, eeeeeee eeee Me8M, eeeeeeee eeeeeee e eee ee Meeeee, eee eeeeeeee ee eeeee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:88); eeeee: 888ee (88%).

References