SMARTS: [#6;c,$(C(=O)O),$(C#N):3][#6;H1:2]=[#6;H2:1].[#6;$([#6]=[#6]),$(c:c):4][Cl,Br,I]>>[#6:4]/[#6:1]=[#6:2]/[#6:3]
Conditions
Reactant 2: unsaturated halide.
R1: aryl, COO, CN. R2: aryl, vinyl. X: Cl, Br, I.
References
Heck, R. F.
J. Am. Chem. Soc.,
1968, 90, 5518–5526.
Heck, R. F.; Nolley, J. P.
J. Org. Chem.,
1972, 37, 2320–2322.
Dieck, H. A.; Heck, R. F.
J. Am. Chem. Soc.,
1974, 96, 1133–1136.
M. L. Kantam, P. Srinivas, J. Yadav, P. R. Likhar, S. Bhargava,
J. Org. Chem.,
2009, 74, 4882-4885.
Other sources
Organic chemistry
Wikipedia