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Synlett 2024; 35(04): 394-404
DOI: 10.1055/a-2106-1585
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11th Singapore International Chemistry Conference (SICC-11)

Sustainable Organocatalytic Processes to Access Alkyl SuFEx Click Hubs and Tetrasubstituted Carbon Centers: Potential Libraries for Multidisciplinary Applications

Woo Hee Kim
,
Jin Hyun Park
,
Sun Bu Lee
,
Muhammad Israr
,
Byeong Jun Koo
,
Soo Bok Kim
,
Soyeon Kim
,
Han Yong Bae∗
Generous support from the Ministry of Science, ICT and Future Planning of Korea (2020R1C1C1006440, 2021R1A2C2093597, and 2019R1A6A1A10073079) is acknowledged. This work was also supported by the Institute of Civil-Military Technology Cooperation funded by the Defense Acquisition Program Administration and Ministry of Trade, Industry and Energy, Korean Government (20-CM-BR-05).
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This Account is dedicated to Prof. Dr. Benjamin List (Max-Planck-Institut für Kohlenforschung) and the Department of Chemistry of Sungkyunkwan University on the occasion of its 70th anniversary.

Abstract

In this Account, we provide an overview of our recent achievements on sustainable organocatalysis. Our group has unveiled the effectiveness of specific organocatalysts under various environmentally benign conditions. We have found that N-heterocyclic carbene and phosphazene superbases exhibit favorable performances in bulk aqueous reaction environments. In addition, the use of organic superacid catalysts results in synergistic effects when hydrogen-bond donor catalysts are assembled in aqueous media. Moreover, we discovered that a neutral organic salt precatalyst can generate a potent silylium Lewis acid catalyst in situ, specifically under solvent-free conditions. These innovative, sustainable organocatalytic processes have successfully facilitated the conversion of raw starting materials into valuable compounds, including sulfur(VI) fluoride exchange (SuFEx) click hubs and tetrasubstituted carbon centers incorporating heteroatoms.

1 Introduction

2 Water-Accelerated N-Heterocyclic Carbene (NHC) Catalysis for β-Aminosulfonyl Fluorides

3 Water-Accelerated Phosphazene Superbase Catalysis for β-Sulfidosulfonyl Fluorides and γ-Geminal Dithioester-Incorporated Sulfonyl Fluorides

4 Water-Accelerated Synergistic Superacid Catalysis for α-Tertiary Amines

5 Solvent-, Metal-, and Purification-Free PPM (parts per million) Neutral Organic Salt Catalysis for Tertiary Cyanohydrin Derivatives

6 Conclusion

Key words

organocatalysis - sustainable process - on-water - solvent-free - sulfur(VI) fluoride exchange (SuFEx) - tetrasubstituted carbon centers


Publication History

Received: 13 May 2023

Accepted after revision: 05 June 2023

Accepted Manuscript online:
05 June 2023

Article published online:
19 July 2023

© 2023. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

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