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Keywords:

  • alcohols;
  • alkynes;
  • isotopic labeling;
  • gold;
  • reaction mechanisms

Abstract

Under the conditions of dual activation catalysis with oxygen nucleophiles, β-substituted naphthalenes were obtained from 1,2-diethinyl arenes. Mechanistic studies, which include isotope labeling experiments, support that dual activation leads to β-substituted naphthalenes, whereas α-naphthalenes are formed by π activation only, and no gold acetylide or dual activation is involved in the formation of the α-substituted products. Additional experiments on substrates that led to dibenzopentalenes support these mechanistic insights.