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Cs 2 CO 3 Catalyzed Intramolecular Aminocarbonylation of Alkynes: Synthesis of 3‐Amino‐1 H ‐inden‐1‐ones from N ‐ tert ‐Butyl‐2‐(1‐alkynyl)benzaldimines
Author(s) -
Guo Zhen,
Liu Tao,
Liang Xiujuan,
Wu Yuting,
Yao Tuanli
Publication year - 2020
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.201901349
Subject(s) - chemistry , intramolecular force , catalysis , medicinal chemistry , methylene , transition metal , alkyne , reaction conditions , stereochemistry , organic chemistry
Synthesis of a wide variety of 3‐amino‐1 H ‐inden‐1‐ones from N ‐ tert ‐butyl‐2‐(1‐alkynyl)benzaldimines via intramolecular aminocarbonylation of alkynes using Cs 2 CO 3 as catalyst and air as oxidant has been developed. This highly atom‐efficient, transition‐metal‐free reaction proceeds under thermal conditions. We propose that the reaction proceeds through an unprecedented 5‐ exo ‐ dig cyclization of N ‐ tert ‐butyl‐2‐(1‐alkynyl)benzaldimines and thermal rearrangement of 3‐methylene‐2λ 2 ‐isoindolin‐1‐ols.
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