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. Author manuscript; available in PMC: 2011 Jun 4.
Published in final edited form as: Org Lett. 2010 Jun 4;12(11):2622–2625. doi: 10.1021/ol100824f

Table 1.

Borostannylation of Alkynes Using 1 Followed by Dioxaborolidene Formationa

entry alkyne adduct (%yield)b
1. graphic file with name nihms204940t1.jpg
2a
graphic file with name nihms204940t2.jpg
4a (83)
2. graphic file with name nihms204940t3.jpg
2b
graphic file with name nihms204940t4.jpg
4b (82)
3. graphic file with name nihms204940t5.jpg
2c
graphic file with name nihms204940t6.jpg
4c (81)
4. graphic file with name nihms204940t7.jpg
2d
graphic file with name nihms204940t8.jpg
4d (80)
5. graphic file with name nihms204940t9.jpg
2e
graphic file with name nihms204940t10.jpg
4e (80)
6. graphic file with name nihms204940t11.jpg
2f
graphic file with name nihms204940t12.jpg
4f (84)
7. graphic file with name nihms204940t13.jpg
2g
graphic file with name nihms204940t14.jpg
8. graphic file with name nihms204940t15.jpg
2hc
graphic file with name nihms204940t16.jpg
a

see Scheme 1 for procedure.

b

isolated by column chromatography.

c

use of PdCl2(CH3CN)2/P(But)3 (60 °C, 12 h) gives a ratio of 4h1: 4h2 = 94:6.