Friedel‐Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines DOI Creative Commons

Ming-Kai Wei,

Ze‐Xin Zhang, Mingyan Ding

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 11, 2024

Abstract Sulfur functional groups are ubiquitous in molecules used the pharmaceutical and agrochemical industries, within these collections sulfones hold a prominent position. The double aza‐analogues of sulfones, sulfondiimines, offer significant potential discovery chemistry but to date their applications have been limited by lack convenient synthetic routes. existing methods mainly rely on imination low‐valent‐sulfur intermediates, or combination pre‐formed organometallic reagents electrophilic S(VI)‐functionalities. Herein, we describe Friedel–Crafts‐type reaction sulfondiimidoyl fluorides with (hetero)aryls. This new SuFEx reactivity benefits from broad group tolerance, mild conditions, does not require use reagents. efficient unprotected indoles pyrroles, as well furan, thiophene carbocyclic aromatics, further demonstrates advantages reactions. We show that can be tuned switching N ‐substituents, allowing an expansion range coupling partners. utility transformation is exemplified synthesis sulfondiimine analogue HIV‐I reverse transcriptase‐inhibitor L‐737,126.

Language: Английский

A Practical Guide to SuFEx Chemistry: An Overview of S(VI)-SuFEx Linkers and their Reactivity DOI Creative Commons
Renzo Luisi, Michael Andresini, Philipp Natho

et al.

Synthesis, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 5, 2024

Abstract Sulfur(VI)–fluoride exchange (SuFEx) is a second generation, metal-free click chemistry concept introduced by Sharpless in 2014. Since the introduction of concept, large variety synthetic methodologies to S(VI)-SuFEx hubs, and their derivatization with oxygen-, nitrogen-, carbon-based nucleophiles have been developed. Herein, we provide concise practical overview for preparation, SuFExability, inclusive which substituents are tolerated. The stereoselective synthesis aza-derivatives also discussed. 1 Introduction 2 Synthesis SuFEx Hubs 2.1 Sulfonyl Fluorides 2.2 Fluorosulfates 2.3 Sulfamoyl 2.4 Sulfonimidoyl 2.5 Sulfuramidimidoyl Sulfurofluoridoimidates 2.6 Sulfondiimidoyl 3 Reactivity 3.1 3.2 3.3 3.4 3.5 3.6 4 Stereochemical Considerations Chemistry 5 Conclusion Outlook

Language: Английский

Citations

1
Friedel‐Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines DOI Creative Commons

Ming-Kai Wei,

Ze‐Xin Zhang, Mingyan Ding

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 11, 2024

Abstract Sulfur functional groups are ubiquitous in molecules used the pharmaceutical and agrochemical industries, within these collections sulfones hold a prominent position. The double aza‐analogues of sulfones, sulfondiimines, offer significant potential discovery chemistry but to date their applications have been limited by lack convenient synthetic routes. existing methods mainly rely on imination low‐valent‐sulfur intermediates, or combination pre‐formed organometallic reagents electrophilic S(VI)‐functionalities. Herein, we describe Friedel–Crafts‐type reaction sulfondiimidoyl fluorides with (hetero)aryls. This new SuFEx reactivity benefits from broad group tolerance, mild conditions, does not require use reagents. efficient unprotected indoles pyrroles, as well furan, thiophene carbocyclic aromatics, further demonstrates advantages reactions. We show that can be tuned switching N ‐substituents, allowing an expansion range coupling partners. utility transformation is exemplified synthesis sulfondiimine analogue HIV‐I reverse transcriptase‐inhibitor L‐737,126.

Language: Английский

Citations

1
Friedel‐Crafts Reactivity with Sulfondiimidoyl Fluorides for the Synthesis of Heteroaryl Sulfondiimines DOI Creative Commons

Ming-Kai Wei,

Ze‐Xin Zhang, Mingyan Ding

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 11, 2024

Abstract Sulfur functional groups are ubiquitous in molecules used the pharmaceutical and agrochemical industries, within these collections sulfones hold a prominent position. The double aza‐analogues of sulfones, sulfondiimines, offer significant potential discovery chemistry but to date their applications have been limited by lack convenient synthetic routes. existing methods mainly rely on imination low‐valent‐sulfur intermediates, or combination pre‐formed organometallic reagents electrophilic S(VI)‐functionalities. Herein, we describe Friedel–Crafts‐type reaction sulfondiimidoyl fluorides with (hetero)aryls. This new SuFEx reactivity benefits from broad group tolerance, mild conditions, does not require use reagents. efficient unprotected indoles pyrroles, as well furan, thiophene carbocyclic aromatics, further demonstrates advantages reactions. We show that can be tuned switching N ‐substituents, allowing an expansion range coupling partners. utility transformation is exemplified synthesis sulfondiimine analogue HIV‐I reverse transcriptase‐inhibitor L‐737,126.

Language: Английский

Citations

0