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. Author manuscript; available in PMC: 2012 May 28.
Published in final edited form as: Chem Commun (Camb). 2011 Apr 12;47(20):5717–5719. doi: 10.1039/c1cc11087j

Table 2.

Representative benzylic-alkenyl cross-couplingsa

graphic file with name nihms315032u2.jpg
Entry Product (Yield)b Entry Product (Yield)b
1 graphic file with name nihms315032t1.jpg
2 (82%)		 2 graphic file with name nihms315032t2.jpg
3 (91%)
graphic file with name nihms315032t3.jpg graphic file with name nihms315032t4.jpg
3 4 R = CF3 (84%) 5 6 R = H (95%)
4 5 R = Cl (89%) 6 7 R = OMe (81%)
7 graphic file with name nihms315032t5.jpg
8 (90%)		 8 graphic file with name nihms315032t6.jpg
9 (85%) E/Z 83/17c
9 graphic file with name nihms315032t7.jpg
10 (77%) E/Z 92/8d 		10 graphic file with name nihms315032t8.jpg
11 (95%)
11 graphic file with name nihms315032t9.jpg
12 (92%)		 12 graphic file with name nihms315032t10.jpg
13 (96%)
13 graphic file with name nihms315032t11.jpg
14 (83%)		 14 graphic file with name nihms315032t12.jpg
15 (79%)e
15 graphic file with name nihms315032t13.jpg
16 (82%)
a

Conditions: benzylic chloride (2–3 mmol), alkenyl halide (X = I, for entries 1–6, 10, 12, 15, and X = Br for entries 7–9, 11, 13–14; 1 mmol), zinc dust (3–4 mmol), PdCl2(Amphos)2 (0.02 mmol), degassed water (3 mL), rt, 6 h.

b

Isolated yield.

c

From commercially available β-bromo-styrene, E/Z = 87/13.

d

From commercially available (2-bromovinyl)trimethylsilane, E/Z = 93/7.

e

From commercially available 90% technical grade a-bromostyrene.