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Stanforth, S. P., Science of Synthesis, (2007) 31, 106.
The palladium-catalyzed synthesis of arylalkenes from haloarenes and alkenes (the Heck reaction) is the subject of several reviews.[127–131] 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[888–888]
M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
M | MM8Me | 8.8 eee% [Me8(eee)8], 8 eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888–888°M | 88 | [888] |
8-MMe | MM8Me | 8.8 eee% [Me8(eee)8], 8 eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888–888°M | 88 | [888] |
8-MMM | MM8Me | 8 eee% Me(MMe)8, 8 eee% Me8M, MeMMe, MMM, 888–888°M | 88 | [888] |
M | Me | 8.8 eee% [Me8(eee)8], 8 eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888–888°M | 88 | [888] |
8-MMM | Me | 8.8 eee% [Me8(eee)8], 8 eee% e-Me8M, Me8MM8, 8,8-eeeeeee, 888–888°M | 88 | [888] |
8-MMM | Me | 8 eee% Me(MMe)8, 8 eee% eeeeee, MeMMe, MMM, 888°M | 88 | [888] |
8-MM8 | Me | 8 eee% Me(MMe)8, 8 eee% 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 (888 ee, 8.888 eeee) ee 8,8-eeeeeee (8.8 eM) eee e eeee ee e-Me8M (88.8 ee, 8.888 eeee) ee 8,8-eeeeeee (8.88 eM) eeee eeeee ee eeee ee e Meeeeee eeee eeeeeeeeee e eeeeeeee eeeeeee eee, [Me8(eee)8] (88.8 ee, 8.888 eeee), eee Me8MM8 (888 ee, 8.88 eeee). Meeeee eeeeeeee (888 ee, 8.88 eeee) eee eeee eeeee ee eeeeeee. Mee eeeeee Meeeeee eeee eee eeeeee ee ee eee eeee ee 888°M eee eee eeeeeee eee eeeeeee eee 88 e. 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: 888 ee (88%).
References
[106] | Meeeee, M. M.; Me, M. M., Meeee. Meee., (8888) 888, 8888; Meeee. Meee. Mee. Me., (8888) 88, 8888. |
[107] | Meeeee, M. M.; Meeeeee, M.; Me, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[127] | Meee, M. M., Mee. Meeee. (M. M.), (8888) 88, 888. |
[128] | Meeeeee, M. M.; Meeee, M., Meee. Mee., (8888) 88, 8888. |
[129] | Meeeeeeee, M. M.; Meee, M.; Meeeee, M., Mee. Meeee., (8888) 8, 888. |
[130] | Meeeeeeeee, M. M.; Meeeeeeee, M. M., Meee. Mee., (8888) 888, 8888. |
[131] | Meeeeeeee, M. M.; Mee, M. M.; Meeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
[132] | Meeeeee, M.; Mee-Meeee, M.; Meeeeeee, M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
[133] | Meeeee, M. M.; Meee, M. M., M. Me. Meee. Mee., (8888) 888, 8888. |
[134] | Meeeee, M. M.; Me, M. M., M. Mee. Meee., (8888) 88, 88. |
[135] | Meeeeeee, M. M.; Meeeeeee, M.; Öeeee, M.; Meeeee, M.; Meeeeee, M., M. Mee. Meeee. M: Meee., (8888) 888, 888. |
[136] | Mee-Meeee, M.; Meeeeee, M.; Meeee, M.; Meeeeeee, M., Meeeeeeeeeeeeee, (8888) 88, 8888. |
[137] | Meee, M.; Meeeee, M., Meee.–Mee. M., (8888) 8, 8888. |
[138] | Meee, M. M., Mee. Meeee. (M. M.), (8888) 88, 888. |
[139] | Meeeeee, M.; Meeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[140] | Meeeeeeee, M.; Meeeeeee, M.; Meeeee, M., M. Meee. Mee., Meeeee Meeee. 8, (8888), 8888. |
[141] | Meeeeee, M.; Meeeee, M., Mee. Meee. Mee., (8888) 88, 888. |