Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles

Mete, Trimbak B.; Khopade, Tushar M.; Bhat, Ramakrishna G.

doi:10.1016/j.tetlet.2016.12.043

Cited by 50 publications

(21 citation statements)

References 36 publications

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“…Lots of available methods of thiocyanation have combined thiocyanate salts with chemical oxidants such as CAN, 4 oxone, 5 DDQ, 6 Cu/O 2 , 7 hypervalent iodine reagents, 8,9 Mn(OAc) 3 , 10 K 2 S 2 O 8 , 11,12 etc. (Scheme 1a) Despite their efficiencies, these approaches suffered from many drawbacks and limitations: harsh oxidizing experimental procedures, the use of stoichiometric oxidants and the bad impact of heavy-metal wastes.…”

Section: Introductionmentioning

confidence: 99%

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

et al. 2018

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A low-cost and efficient thio-and selenocyanation strategy for electron-rich arenes has been developed under constant-current electrolytic conditions in an undivided cell. This strategy is versatile for various (hetero)aromatic compounds such as indole, pyrrole, aniline and anisole under mild conditions without any catalyst or oxidant. Readily available salts NH 4 SCN and KSeCN are employed respectively as the sole reagent.

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Section: Introductionmentioning

confidence: 99%

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

et al. 2018

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“…The corresponding alcohols 8a , 8d , and 8e were also isolated in yields of 12–22%, whereas cyclohexanol ( 8b ) was only obtained as part of a complex mixture. In the case of 6c , benzophenone ( 8c ) was isolated in 51% yield 14 along with nitroalkane 7c .…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Phae-nok¹,

Kuhakarn²,

Leowanawat³

et al. 2022

Synlett

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Decarboxylative transformations of paraconic acids, a class of γ-butyrolactones containing a carboxylic acid group at the β position as their characteristic functionality, using a combination of AgNO3/K2S2O8 was investigated. The dual function of AgNO3 as an initiator for decarboxylation process and a nitrogen dioxide radical source that reacts with aliphatic carboxylic substrates of this study was reported for the first time. Starting from paraconic acids, β-nitro- and β-hydroxy γ-butyrolactones were obtained in good combined yields (41-85% yields) with moderate selectivity in one-pot operation. The reactions completed within acceptable reaction time (2 h) under mild reaction conditions that γ-butyrolactone core could be tolerated. The present study represents the direct and site-specific entry to β-nitro- and β-hydroxy γ-butyrolactones which are important precursors in organic transformations.

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“…The chemical approach has been actively developed over the past 10–15 years, but it is often associated with the use of an excess of unrecyclable oxidants, which can sometimes be toxic, scalding or poorly available (e.g., Br 2 [ 98 ], I 2 [ 99 ], DEAD [ 100 ], HIO 3 [ 101 ], H 5 IO 6 [ 102 ], I 2 O 5 [ 103 ], H 2 O 2 [ 102 , 104 , 105 , 106 , 107 ], K 2 S 2 O 8 [ 108 , 109 ], CAN [ 110 ], Mn(OAc) 3 [ 111 ], p -TSA [ 112 ], NCS [ 113 ], NBS [ 100 ], NIS [ 114 ], NTS [ 115 ], DDQ [ 116 , 117 ]). The electrochemical approach (see [ 22 ], Scheme 3 , route II b , and Scheme 13 ) is devoid of such disadvantages, but it is poorly studied in general [ 118 , 119 , 120 ].…”

Section: Electrooxidative C–h Thiocyanation Of 5-aminopyrazoles and Pyrazolo [15-a]pyrimidinesmentioning

confidence: 99%

Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds

et al. 2021

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The review summarizes for the first time the poorly studied electrooxidative functionalization of pyrazole derivatives leading to the C–Cl, C–Br, C–I, C–S and N–N coupling products with applied properties. The introduction discusses some aspects of aromatic hydrogen substitution. Further, we mainly consider our works on effective synthesis of the corresponding halogeno, thiocyanato and azo compounds using cheap, affordable and environmentally promising electric currents.

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Transition-metal-free regioselective thiocyanation of phenols, anilines and heterocycles

Cited by 50 publications

References 36 publications

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

A low-cost electrochemical thio- and selenocyanation strategy for electron-rich arenes under catalyst- and oxidant-free conditions

Decarboxylation of Paraconic Acids by a Silver(I) Nitrate/Persulfate Combination: An Entry to β-Nitro- and β-Hydroxy γ-Butyrolactones

Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds

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