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. Author manuscript; available in PMC: 2013 Mar 16.
Published in final edited form as: Org Lett. 2012 Feb 29;14(6):1416–1419. doi: 10.1021/ol3001552

Table 2.

Ni-Catalyzed Allylic Boronate Synthesis from Allylic Acetates.

graphic file with name nihms360655u3.jpg
entry substrate product yield (%)a
1 graphic file with name nihms360655t1.jpg graphic file with name nihms360655t2.jpg 92
2 graphic file with name nihms360655t3.jpg graphic file with name nihms360655t4.jpg 84b
3 graphic file with name nihms360655t5.jpg graphic file with name nihms360655t6.jpg 94
4 graphic file with name nihms360655t7.jpg graphic file with name nihms360655t8.jpg 96
5 graphic file with name nihms360655t9.jpg graphic file with name nihms360655t10.jpg 92
6 graphic file with name nihms360655t11.jpg graphic file with name nihms360655t12.jpg 95
7 graphic file with name nihms360655t13.jpg graphic file with name nihms360655t14.jpg 52d
8 graphic file with name nihms360655t15.jpg graphic file with name nihms360655t16.jpg 70e
9 graphic file with name nihms360655t17.jpg graphic file with name nihms360655t18.jpg 93c,e
a

Isolated yield of purified material. Value is an average of two experiments.

b

Contains ca. 5% impurity.

c

Employed 10% catalyst and PPh3.

d

Employed 10% catalyst.

e

Product is a 2:1 ratio of E:Z isomers as established by NMR.