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. Author manuscript; available in PMC: 2012 Feb 4.
Published in final edited form as: Org Lett. 2010 Dec 21;13(3):394–397. doi: 10.1021/ol102682r

Table 2.

CDR of rac-1 and Negishi arylation or vinylation

graphic file with name nihms260166t2.jpg
entry electrophile product yield
(%)
er
(R:S)
1a graphic file with name nihms260166t3.jpg graphic file with name nihms260166t4.jpg 63 92:8
2a,b graphic file with name nihms260166t5.jpg graphic file with name nihms260166t6.jpg 59 6:94
3a graphic file with name nihms260166t7.jpg graphic file with name nihms260166t8.jpg 75 97:3
4a graphic file with name nihms260166t9.jpg graphic file with name nihms260166t10.jpg 69 95:5
5a graphic file with name nihms260166t11.jpg graphic file with name nihms260166t12.jpg 64 92:8
6a graphic file with name nihms260166t13.jpg graphic file with name nihms260166t14.jpg 60 91:9
7a,c graphic file with name nihms260166t15.jpg graphic file with name nihms260166t16.jpg 66 90:10
8a graphic file with name nihms260166t17.jpg graphic file with name nihms260166t18.jpg 60 93:7
9e graphic file with name nihms260166t19.jpg graphic file with name nihms260166t20.jpg 67 97:3
10d graphic file with name nihms260166t21.jpg graphic file with name nihms260166t22.jpg 46 88:12
11b,d graphic file with name nihms260166t23.jpg graphic file with name nihms260166t24.jpg 51 10:90
12d graphic file with name nihms260166t25.jpg graphic file with name nihms260166t26.jpg 50 93:7
13d graphic file with name nihms260166t27.jpg graphic file with name nihms260166t28.jpg 53 85:15
14a graphic file with name nihms260166t29.jpg graphic file with name nihms260166t30.jpg 63 92:8
15a,e graphic file with name nihms260166t31.jpg graphic file with name nihms260166t32.jpg 66 93:7
a)

stirred at rt for 18 h during step (iv),

b)

CDR using (S,R)-2;

c)

the aryl bromide contained a small amount of 2-bromobenzonitrile leading to formation of the ortho cyano constitutional isomer in 90:10 er;

d)

stirred at 60 °C for 22 h during step (iv),

e)

a small amount of the Z-alkene was obtained as a minor isomer in 92:8 er.