Helicene synthesis by Brønsted acid-catalyzed cycloaromatization in HFIP [(CF3)2CHOH]
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A facile synthesis of carbo- and heterohelicenes was achieved via tandem cycloaromatization of bisacetal precursors, which were readily prepared through C–C bond formation by Suzuki–Miyaura coupling. This cyclization was efficiently realized by a catalytic amount of trifluoromethanesulfonic acid (TfOH) in a cation-stabilizing solvent, 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP), which readily allowed gram-scale syntheses of higher-order helicenes, double helical helicenes, and heterohelicenes.
2011 ◽
Vol 353
(17)
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pp. 3139-3145
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2016 ◽
Vol 2017
(2)
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pp. 262-265
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2012 ◽
Vol 355
(1)
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pp. 87-92
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2007 ◽
Vol 48
(14)
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pp. 2611-2615
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2011 ◽
Vol 44
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pp. 1156-1171
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