Lewis Acid Enhancement of Gold Catalytic Activity Through Counterion Coordination. Synthesis of Benzofulvenes from Progargylsilanes and Benzophenones. Issue 7 (11th March 2022)

• Record Type: Journal Article
• Authors: Fernández, Sergio; Santamaría, Javier; Ballesteros, Alfredo
• Is Part Of: Advanced synthesis & catalysis. Volume 364:Issue 7(2022)
• Page Start: 1286
• Page End: 1294
• Publication Date: 2022-03-11
• Subjects: Gold -- Homogeneous catalysis -- Lewis acids -- Anions -- Synthetic methods; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.202200165
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A simple, regioselective and high yielding gold‐catalyzed synthesis of benzofulvenes, from progargylsilanes and benzophenones, is described. Initially, the carbonyl compound is synergistically activated by the silyl moiety and, for the cyclization step, the gold catalytic activity is clearly increased by the participation of aluminum trichloride, acting as a cocatalyst. Several mechanistic intermediates, such as enynes and silylbenzofulvenes, have been isolated. Different control experiments have been performed, indicating the participation of [LAu][NTf2 AlCl3 ] complex as the true catalyst, and revealing a dramatic enhancement of the gold activity by coordination of the Lewis acid to the gold counterion. Abstract :