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. 2013 May 17;52(24):6283–6287. doi: 10.1002/anie.201301167

Table 2.

Selective carbocyclization of allenynes 1 yielding borylated trienes 4[a]

Inline graphic

Entry Allenyne Product 4/5[b] Yield of4[%],[c] ratio[b]
1 Inline graphic Inline graphic 10:1 73
2 Inline graphic Inline graphic 99:1 92
3 Inline graphic Inline graphic 99:1 55 4 c/4 c′=2.4:1
Inline graphic
4 Inline graphic Inline graphic 9:1 >11:1 81 92[d]
5 Inline graphic Inline graphic 18:1 65 4 e/4 e′=2.3:1
Inline graphic
6 Inline graphic Inline graphic 5:1 48 4 f/4 f′=1.4:1
Inline graphic
7 Inline graphic Inline graphic >20:1 57
[a]

Unless otherwise noted, 1 (0.1–0.2 mmol), B2pin2 (1.3 equiv), Pd(OAc)2 (2 mol %), BQ (1.1 equiv), and LiOAc⋅2 H2O (20 mol %) were dissolved in DCE (5 mL mmol−1) and stirred at 50 °C for 15 h.

[b]

The ratio was determined by 1H NMR analysis of the reaction mixture.

[c]

Yield of the isolated product.

[d]

1 mmol of 1 d was used. E=CO2Me.