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. Author manuscript; available in PMC: 2013 Jun 19.
Published in final edited form as: J Am Chem Soc. 2008 Jan 4;130(4):1440–1452. doi: 10.1021/ja0773507

Table 9.

Metal-Catalyzed Synthesis of Furans 26

graphic file with name nihms382578u9.jpg

Entry Substrate Cat (mol%) T,°C Product Yield (%)a,b
1 graphic file with name nihms382578t68.jpg Sn(OTf)2 (5) 100 graphic file with name nihms382578t69.jpg 26a 81
2 graphic file with name nihms382578t70.jpg In(OTf)3 (10) 115 graphic file with name nihms382578t71.jpg 26b 64
3 graphic file with name nihms382578t72.jpg In(OTf)3 (5) 100 graphic file with name nihms382578t73.jpg 26c 90
4 graphic file with name nihms382578t74.jpg AgOTf(20) 140 graphic file with name nihms382578t75.jpg 26d 79c
5 graphic file with name nihms382578t76.jpg In(OTf)3 (5) Au(PPh3)OTf(2) 100 graphic file with name nihms382578t77.jpg 26e 72
52d
6 graphic file with name nihms382578t78.jpg In(OTf)3 (5) Au(PPh3)OTf (1) ″ graphic file with name nihms382578t79.jpg 26f 88e
graphic file with name nihms382578t80.jpg 26g 76df
7 graphic file with name nihms382578t81.jpg In(OTf)3 (5) ″ graphic file with name nihms382578t82.jpg 26h 75
8 graphic file with name nihms382578t83.jpg ″ ″ graphic file with name nihms382578t84.jpg 26i 18d
9 graphic file with name nihms382578t85.jpg ″ ″ graphic file with name nihms382578t86.jpg 26j 10d
10 graphic file with name nihms382578t87.jpg ″ ″ graphic file with name nihms382578t88.jpg 26k 62
11 graphic file with name nihms382578t89.jpg In(OTf)3 (5) Au(PPh3)OTf(l) ″ graphic file with name nihms382578t90.jpg 26l 93
89
12 graphic file with name nihms382578t91.jpg Sn(OTf)2 (5) ″ graphic file with name nihms382578t92.jpg 26m 85
13 graphic file with name nihms382578t93.jpg ″ ″ graphic file with name nihms382578t94.jpg 26n 94
a

Isolated yield.

b

Reactions were performed on 0.25–0.8 mmol scale.

c

p-Xylene was used as a solvent.

d

NMR yield.

e

Mixture (2.3:1) of 26f: 26g by 1H NMR.

f

Mixture (2.2:1) of 26f:26g by 1H NMR.