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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 48, 2018 - Issue 3
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Original Articles

Secondary amine-catalyzed [3 + 3] benzannulation to access polysubstituted benzenes through iminium activation

, , , , , & show all
Pages 336-343 | Received 31 Aug 2017, Published online: 08 Jan 2018
 

ABSTRACT

An organocatalytic [3 + 3] benzannulation to access polysubstituted benzenes from readily available α,β-unsaturated aldehydes and 1,3-bis(phenylsulfonyl)propene or 4-sulfonylcrotonates is described. The key reaction step is considered to be the iminium activation of enals by a secondary aminocatalyst. This organocatalytic protocol avoids the traditional strategy which is always with the aid of a transition-metal or a stoichiometric amount of strong base, and allows the synthesis of trisubstituted benzenes in high to excellent yields (74–96%).

GRAPHICAL ABSTRACT

Additional information

Funding

We are grateful to the National Natural Science Foundation of China (21302163) for financial support.

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