Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

Synthesis and Catalytic Activity of 1,2-Benzenediamine-Derived Organocatalysts Based on (1R,2R)-Cyclohexane-1,2-diamine

Luka Ciber
,
Klara Klemenčič
ORCID logo ,
Ana Golob
,
Helena Brodnik
,
Franc Požgan
ORCID logo ,
Jurij Svete
ORCID logo ,
Bogdan Štefane
ORCID logo ,
Uroš Grošelj
* ORCID logo
Version 1 : Received: 29 February 2024 / Approved: 29 February 2024 / Online: 29 February 2024 (20:12:32 CET)

A peer-reviewed article of this Preprint also exists.

Ciber, L.; Klemenčič, K.; Golob, A.; Brodnik, H.; Požgan, F.; Svete, J.; Štefane, B.; Grošelj, U. Synthesis and Catalytic Activity of 1,2-Benzenediamine-Derived Organocatalysts Based on (1R,2R)-Cyclohexane-1,2-Diamine. Catalysts 2024, 14, 274. Ciber, L.; Klemenčič, K.; Golob, A.; Brodnik, H.; Požgan, F.; Svete, J.; Štefane, B.; Grošelj, U. Synthesis and Catalytic Activity of 1,2-Benzenediamine-Derived Organocatalysts Based on (1R,2R)-Cyclohexane-1,2-Diamine. Catalysts 2024, 14, 274.

Abstract

A four-step synthesis of bifunctional, noncovalent organocatalysts based on the chiral (1R,2R)-cyclohexane-1,2-diamine scaffold containing a 1,2-benzenediamine H-bond donor was developed. Nucleophilic aromatic substitution of the 2-fluoronitrobenzene derivative with the commercial (1R,2R)-cyclohexane-1,2-diamine was followed by selective alkylation of the primary amino group, reduction of the aromatic nitro group and final derivatization of the primary aromatic amino group, i.e. acylation, sulfonation, reductive alkylation and arylation, leading to the four subtypes of organocatalysts. All new compounds were fully characterized. The prepared organocatalysts (32 examples) were tested in the Michael addition of acetylacetone to trans-β-nitrostyrene, yielding the addition product with incomplete conversions (up to 93%) and enantioselectivities of up to 41% ee.

Keywords

asymmetric organocatalysis; H-bond donor organocatalysts; (1R,2R)-cyclohexane-1,2-diamine; benzene-1,2-diamines; reduction; nucleophilic aromatic substitution; reductive alkylation; arylation; acylation; sulfonation

Subject

Chemistry and Materials Science, Organic Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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