Metal‐free, Phosphoric Acid‐catalyzed Regioselective 1, 6‐Hydroarylation of para‐Quinone Methides with Indoles in Water. Issue 9 (24th March 2022)

• Record Type: Journal Article
• Authors: Xiong, Biquan; Si, Lulu; Liu, Yu; Xu, Weifeng; Jiang, Tao; Cao, Fan; Tang, Ke‐Wen; Wong, Wai‐Yeung
• Is Part Of: Chemistry, an Asian journal. Volume 17:Issue 9(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-03-24
• Subjects: 1, 6-hydroarylation -- brønsted-acid catalysis -- green media -- indoles -- para-quinone methides; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.202200042
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: An efficient, cheap and green protocol for the highly regioselective 1, 6‐hydroarylation of para ‐quinone methides ( p ‐QMs) with indoles at the C‐3 position has been established by phosphoric acid catalysis in water under transition‐metal‐free reaction conditions. A wide range of indole derivatives and para ‐quinone methides ( p ‐QMs) are compatible for the reaction, affording the corresponding 1, 6‐hydroarylation products with good to excellent yields. The possible mechanism of the reaction has been explored through step‐by‐step control experiments. The protocol is convenient for practical applications, leading to a safe, green and feasible way for the formation of C‐3 diarylmethyl functionalized indole derivatives. Abstract : An efficient, cheap and green protocol for the highly regioselective 1, 6‐hydroarylation of para ‐quinone methides ( p ‐QMs) with indoles at the C‐3 position has been established by phosphoric acid catalysis in water under transition‐metal‐free reaction conditions. The protocol is practical, representing a direct and simple way to produce functionalized α‐diarylmethyl substituted indoles from basic starting materials in good to excellent yields.