Organocatalytic Silicon-Free SuFEx reactions for modular synthesis of sulfonate esters and sulfonamides

Sulfur(VI) fluoride exchange (SuFEx) click chemistry provides a powerful tool for rapid construction of modular connections. Here, we report a novel catalytic silicon-free SuFEx reaction with sulfonyl fluorides. Under the catalysis of 10 mol% N-heterocyclic carbene (NHC), a range of phenols and alcohols react with different sulfonyl fluorides to afford sulfonate esters in 49-99% yields. In addition, Under the relay catalysis of 10 mol% N-heterocyclic carbene and 10 mol% 1-hydroxybenzotriazole (HOBt), a variety of primary and secondary amines react with different sulfonyl fluorides to produce sulfonamides in 58%-99% yields. More than 140 sulfonylated products, including 17 natural product derivatives have been prepared through this method. Mechanism study showed that NHCs might act as a carbon-centered Brønsted base to catalyse the SuFEx click reactions via the formation of hydrogen bonding with phenols or alcohols.

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Modular synthesis of glycopolymers with well-defined sugar units in the side chain via Ugi reaction and click chemistry: hetero vs. homo

Polymer Chemistry ◽

10.1039/c6py00734a ◽

2016 ◽

Vol 7 (25) ◽

pp. 4263-4271 ◽

Cited By ~ 23

Author(s):

Lulu Xue ◽

Xinhong Xiong ◽

Kui Chen ◽

Yafei Luan ◽

Gaojian Chen ◽

...

Keyword(s):

Click Chemistry ◽

Ugi Reaction ◽

Side Chain ◽

Click Reactions ◽

Modular Synthesis

Modularized glycopolymers were prepared via Ugi and click reactions, and used as models to investigate their binding abilities.

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The dimerization of ammonia and amines

Proceedings of the Royal Society of London Series A - Mathematical and Physical Sciences ◽

10.1098/rspa.1950.0038 ◽

1950 ◽

Vol 200 (1063) ◽

pp. 566-572 ◽

Cited By ~ 46

Keyword(s):

Hydrogen Bonding ◽

Virial Coefficients ◽

Secondary Amines ◽

Tertiary Amines ◽

Second Virial Coefficients ◽

Primary And Secondary Amines

The second virial coefficients of ammonia and the vapours of the primary, secondary and tertiary methylamines and ethylamines have been measured at temperatures between 20 and 130° C. The results are interpreted as showing that dimerization occurs with ammonia and with the primary and secondary amines, but not with the tertiary amines. The dimerization is attributed to hydrogen bonding, and the energy of the N—H....N bond is discussed.

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Hydrogen Bonding and Cation Coordination Effects in Primary and Secondary Amines Dissolved in Carbon Tetrachloride

The Journal of Physical Chemistry A ◽

10.1021/jp066095u ◽

2007 ◽

Vol 111 (14) ◽

pp. 2662-2669 ◽

Cited By ~ 5

Author(s):

Nathalie Rocher ◽

Roger Frech

Keyword(s):

Hydrogen Bonding ◽

Carbon Tetrachloride ◽

Secondary Amines ◽

Primary And Secondary Amines ◽

Cation Coordination

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Reaction of arylmethylenemalonaldehydes with some nucleophiles

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19872699 ◽

1987 ◽

Vol 52 (11) ◽

pp. 2699-2709 ◽

Cited By ~ 3

Author(s):

Dalimil Dvořák ◽

Zdeněk Arnold

Keyword(s):

Inorganic Anions ◽

Secondary Amines ◽

Tertiary Amines ◽

Primary And Secondary Amines ◽

Dipolar Structure

Reaction of arylmethylenemalonaldehydes with tributylphosphine and tertiary amines affords compounds of dipolar structure whereas reaction with primary and secondary amines leads to 1,4-addition products. Salts of nucleophilic inorganic anions add to arylmethylenemalonaldehydes under formation of salts of substituted malonaldehydes.

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Some 1-substitution derivatives of 4-aryl-2,3-dihalogeno-1-naphthols

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19840110 ◽

1984 ◽

Vol 49 (1) ◽

pp. 110-121 ◽

Cited By ~ 1

Author(s):

Jiří Křepelka ◽

Drahuše Vlčková ◽

Milan Mělka

Keyword(s):

Thionyl Chloride ◽

Oxirane Ring ◽

Secondary Amines ◽

Two Phase ◽

Lytic Effect ◽

Primary And Secondary Amines ◽

Phase Medium ◽

Chloro Derivatives ◽

Derivatives Of

Alkylation of derivatives of 4-aryl-1-naphthols (I-V) by 2,3-epoxypropyl chloride in methanolic sodium hydroxide gave epoxy derivatives VI, VIII, IX, XI and XII, apart from products of cleavage of the oxirane ring, VII and X. Analogous alkylation of compounds I, IV and V by 2-(N,N-diethylamino)ethyl chloride hydrochloride in a two-phase medium afforded basic ethers XIII to XV. The cleavage of the oxirane ring in compound VI by the action of primary and secondary amines, piperidine and substituted piperazines led to compounds XVI-XXIV. Reaction of thionyl chloride with compounds XXI, XXII and XXIV gave chloro derivatives XXV-XXVII.Exposure of compound XXII to 4-methylbenzenesulfonyl chloride produced compound XXVIII, retaining the secondary alcoholic group. In an antineoplastic screening in vivo none of the compounds prepared had an appreciable activity. Compound XVII, being an analogue of propranolol, was used in the test of isoproterenolic tachycardia, and showed a beta-lytic effect comparable with that of propranol.

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