Gold‐Catalyzed One‐Pot Synthesis of 1, 3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes. Issue 21 (25th September 2019)

• Record Type: Journal Article
• Authors: Lustosa, Danilo M.; Clemens, Simon; Rudolph, Matthias; Hashmi, A. Stephen K.
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 21(2019)
• Page Start: 5050
• Page End: 5056
• Publication Date: 2019-09-25
• Subjects: Aldehydes -- Alkynes -- Gold -- Deuterium -- Reaction mechanisms; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201900824
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A new and facile one‐pot synthesis of 1, 3‐disubstituted allenes, using cheap and readily available terminal alkynes, benzaldehyde derivatives and morpholine, was developed. A small library of 20 allenes demonstrates a broad applicability, with yields up to 86%. Isotopic‐labelling and cross‐over experiments strongly indicate that our reaction proceeds via a two‐step A 3 ‐coupling followed by a 1, 5‐hydrogen shift process. Abstract :