- One Pot Sequential Synthesis of N-[2-(Phenylsulfinyl)phenyl]acetamides: A Ring Opening Rearrangement Functionalization (RORF)
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A CuII catalyzed one-pot sequential synthesis of N-[2-(phenylthio)phenyl]acetamides from benzo[d]thiazol-2-amines, iodoarenes and carboxylic acids (RCOOH) has been accomplished via ring opening rearrangement functionalization (RORF). Here, the ring opening is associated with the loss of carbon and nitrogen atoms with concurrent S-arylation and N-acylation leading to ortho-bifunctionalized products. A further sequential addition of tert-butyl hydroperoxide (TBHP) results in the formation of a sulfur oxidized product, N-[2-(phenylsulfinyl)phenyl]acetamide. A plausible mechanism has been proposed for this unprecedented ring opening rearrangement functionalization (RORF).
- Behera, Ahalya,Rakshit, Amitava,Sahoo, Ashish K.,Patel, Bhisma K.
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p. 1154 - 1165
(2018/12/13)
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- The synthesis of 2-(Arylthio)arylcyanamides via copper-catalyzed domino intermolecular c-s cross-coupling reaction of 2-aminobenzothiazoles with aryl iodides
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A series of 2-(arylthio)arylcyanamide derivatives were obtained in excellent yields via a copper-catalyzed domino C-S cross-coupling of 2-aminobenzothiazoles with aryl iodides. This reaction occurred via an intermolecular C-S bond formation, associated with C-S bond cleavage, followed by an intermolecular S-arylation under ligand-free conditions. Their structures were unambiguously determined by the analytic tools, such as HRMS, 1H, and 13C NMR analysis.
- Shao, Yin-Lin,Zhang, Xiao-Hong,Han, Jiang-Sheng,Zhong, Ping
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p. 1137 - 1146
(2013/09/23)
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- Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides
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We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl- arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).
- Sahoo, Santosh K.,Jamir, Latonglila,Guin, Srimanta,Patel, Bhisma K.
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experimental part
p. 2538 - 2548
(2010/12/29)
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- Copper-catalyzed domino intra- And intermodular C-S cross-coupling reactions: Synthesis of 2-(Arylthio)arylcyanamides
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Chemical Equation Presented One-pot synthesis of 2-(arylthio)arylcyanamides is accomplished using cheap and air-stable CuSO 4·5H2O as a catalyst by domino intra- and intermolecular C-S cross-coupling reactions of 2-(iodoaryl)thioureas with aryl iodides under ligand-free conditions
- Ramana, Tamminana,Saha, Prasenjit,Das, Manas,Punniyamurthy, Tharmalingam
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supporting information; experimental part
p. 84 - 87
(2010/03/03)
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