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. Author manuscript; available in PMC: 2013 Mar 16.
Published in final edited form as: Org Lett. 2012 Feb 23;14(6):1476–1479. doi: 10.1021/ol300217x

Table 2.

Scope of Ketone Synthesisa

graphic file with name nihms359475u3.jpg
entry 1 2 (R2-X) product yield (%)b
1 1a I-C8H17 (2a) graphic file with name nihms359475t1.jpg
3
86
2c 1b 2a 74
3 1a graphic file with name nihms359475t2.jpg
2c
graphic file with name nihms359475t3.jpg
4
91
4d 1a graphic file with name nihms359475t4.jpg
2d
graphic file with name nihms359475t5.jpg
5
49e
5 1c 2c graphic file with name nihms359475t6.jpg
6
82
6 1d graphic file with name nihms359475t7.jpg
2e
graphic file with name nihms359475t8.jpg
7
78
7 1e 2c graphic file with name nihms359475t9.jpg
8
72
8f 1e 2d graphic file with name nihms359475t10.jpg
9
33
9 1f 2e graphic file with name nihms359475t11.jpg
10
91
10 1f 2c graphic file with name nihms359475t12.jpg
11
67
a

General conditions: 1.5 mmol of 1, 1.0 mmol of 2, 0.05 mmol NiCl2(dme), 0.055 mmol 4,4′-di-tert-butyl-2,2′-bipyridine (dtbpy), 3 mmol Mn, in 2 mL of DMA at 0 °C for 13–30 h.

b

Yield of isolated, purified product.

c

1 Equiv of thioester 1b was used in place of acid chloride 1a and Zn was used in place of Mn.

d

2 Equiv of 1a was used.

e

Product contained a small amount of diethyl succinate, yield of 5 determined by NMR.

f

Run at 30 °C instead of 0 °C.