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Gold‐Catalyzed One‐Pot Synthesis of 1,3‐Disubstituted Allenes from Benzaldehydes and Terminal Alkynes
Author(s) -
Lustosa Danilo M.,
Clemens Simon,
Rudolph Matthias,
Hashmi A. Stephen K.
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900824
Subject(s) - chemistry , benzaldehyde , morpholine , catalysis , terminal (telecommunication) , combinatorial chemistry , organic chemistry , allene , one pot synthesis , telecommunications , computer science
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.