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. Author manuscript; available in PMC: 2017 May 20.
Published in final edited form as: Org Lett. 2016 May 10;18(10):2515–2518. doi: 10.1021/acs.orglett.6b01259

Table 1. Effect of Alkylborane Structure, Catalyst Loading and Oxidant on Reaction Efficiencya.

graphic file with name nihms-784838-t0008.jpg

entry PG BXn oxidant CuX2
(mol %)		 yield
(%)c
1b Cbz BF3K
1a 		MnO2
(2.55 equiv)		 Cu(eh)2
(20 mol %)		 NR
2 Cbz BF3K
1a 		MnO2
(2.55 equiv)		 Cu(OTf)2
(20 mol %)		 82
3 Boc BF3K
1b 		MnO2
(2.55 equiv)		 Cu(OTf)2
(20 mol %)		 46
4 Cbz B(OH)2
1c 		MnO2
(2.55 equiv)		 Cu(OTf)2
(20 mol %)		 52
5d Cbz BF3K
1b 		MnO2
(2.55 equiv)		 Cu(OTf)2
(15 mol %)		 67
6 Cbz BF3K
1b 		Ag2CO3
(2 equiv)		 Cu(OTf)2
(20 mol %)		 63
a

25 mol % 1,1-phenanthroline was used unless otherwise noted.

b

1,10-phenanthroline was not used.

c

Isolated yield.

d

20 mol % 1,10-phenanthroline was used. MnO2 (85% by weight) was used in these reactions.