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. 2012 Sep 26;8:1630–1636. doi: 10.3762/bjoc.8.186

Table 3.

Substrate scope of the phosphane catalyzed coumarin synthesis.a

graphic file with name Beilstein_J_Org_Chem-08-1630-i003.jpg

Entry Substrate Product Yield (%)b

1 Inline graphic
1
Inline graphic
2
82
2 Inline graphic
3a
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2
80
3 Inline graphic
3b
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4b
c
4 Inline graphic
3c
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4c
96
5 Inline graphic
3d
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4d
88d
6 Inline graphic
3e
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4e
83
7 Inline graphic
3f
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4f
96
8 Inline graphic
3g
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4g
96
9 Inline graphic
3h
Inline graphic
4h
75
10 Inline graphic
3i
Inline graphic
4i
99

aReactions were performed on a 1 mmol scale in 1 mL of methanol at 70 °C for 20 h. 15 min prior to workup, the mixture was quenched by addition of 1,2-dibromoethane (20 μL, 0.23 equiv). bYields of pure isolated material. cNo reaction to coumarin observed; starting material (60%) was reisolated. dReaction performed at 90 °C in a closed vessel.