Gold-Catalyzed Divergent Ring-Opening Rearrangement of Cyclopropenes Enabled by Dichotomous Gold?Carbenes |
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| Authors: | Tingrui Li Yilitabaier Julaiti Xiaopeng Wu Jie Han Dr Jin Xie |
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| Institution: | State Key Laboratory of Coordination Chemistry Jiangsu Key Laboratory of Advanced Organic Materials Chemistry and Biomedicine Innovation Center (ChemBIC) School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210023 P. R. China |
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| Abstract: | The gold-catalyzed ring-opening rearrangement of cyclopropenes affords an efficient route to either polysubstituted naphthols or aryl-substituted furans. Owing to the unique dichotomy of gold?carbenes, this protocol provides a switchable reaction selectivity between naphthols and furans enabled by the use of TFP?Au(MeCN)SbF6 (tri(2-furyl) phosphine) or PNP(AuNTf2)2 (bis(diphenylphosphino)(isopropyl) amine) as catalysts respectively. It is proposed that the gold?carbene intermediate might be involved in the cyclopropene→naphthol rearrangement while the gold-carbocation is more likely to be involved in the cyclopropene→furan rearrangement. |
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| Keywords: | divergence gold catalysis gold?carbene homogeneous catalysis rearrangement |
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