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. Author manuscript; available in PMC: 2012 Jun 1.
Published in final edited form as: Org Lett. 2010 Nov 5;12(21):4742–4744. doi: 10.1021/ol101885t

Table 2.

Representative Couplings of Z-Alkenyl Halides in PTS/H2Oa

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entry coupling partners product b Z/Ec
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1 X = I, Y = I (93%)d 99/1
2 X = I, Y = Br (67%)e 96/4
3 X = Br, Y = I (51%)f 95/5
4 X = Br, Y = Br (87%)g 96/4
graphic file with name nihms241656t9.jpg graphic file with name nihms241656t10.jpg
5 X, Y = Br (86%) 97/3
6 X, Y = I (79%) 99/1
graphic file with name nihms241656t11.jpg graphic file with name nihms241656t12.jpg
7 R = H (52%)h 98/2
8 R = n-C5H11 (93%) 97/3
graphic file with name nihms241656t13.jpg graphic file with name nihms241656t14.jpg
9 R = Cl (85%)i 97/3
10 R = C2H5 (90%)i 98/2
graphic file with name nihms241656t15.jpg graphic file with name nihms241656t16.jpg
11 X = Br (94%)d 99/1
12 X = I (95%)d 99/1
graphic file with name nihms241656t17.jpg graphic file with name nihms241656t18.jpg
13 n = 2 (74%) 96/4
14 n = 3 (85%) 99/1
a

Conditions: alkyl halide (2 mmol), alkenyl halide (1 mmol), PdCl2(Amphos)2 (0.01 mmol), zinc dust (3 mmol), TMEDA (2 mmol), 2% PTS/H2O (2 mL), rt, 48 h.

b

Isolated yields.

c

Determined by proton NMR and GC of the crude.

d

12 h.

e

~20% reduction of alkenyl iodide.

f

60% conversion.

g

81% yield with 1.5 equiv of alkyl bromide.

h

GC yield 94%.

i

24 h.