One-pot approach to installing eight-membered rings onto indoles |
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| Authors: | Zhu Can Zhang Xue Lian Xiongdong Ma Shengming |
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| Institution: | State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China. |
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| Abstract: | Ring fusion: The Pd(0)-catalyzed reaction of 2-allyl-3-iodo-1-tosyl-1H-indoles and propargylic bromides affords dihydrocyclooctab]indoles (see scheme; M.S. = molecular sieves, TFP = tris(2-furyl)phosphine, Ts = 4-toluenemethanesulfonyl), and proceeds by carbon-carbon coupling, 1,5]-hydrogen migration, and electrocyclization. The newly established method was used to efficiently access iprindole. |
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| Keywords: | allenes cyclization heterocycles indium palladium |
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