Synergistic Cooperative Effect of Sodium borohydride‐Iodine Towards Cascade C−N and C−S/Se Bond Formation: One‐pot Regioselective Synthesis of 3‐Sulfenyl/selenyl Indoles and Mechanistic Insight

In this work, a new strategy to synthesize 3‐sulfenyl/selenyl indole is reported wherein LC−MS reveals a novel insight into synergistic cooperative effect of NaBH4‐I2 which allows cascade C−N and C−S/C−Se bond formations via reduction‐nucleophilic cyclization‐chalcogenylation, three steps in one‐pot...

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Veröffentlicht in:	Advanced synthesis & catalysis 2018-01, Vol.360 (1), p.180-185
Hauptverfasser:	Lavekar, Aditya G., Equbal, Danish, Saima, Sinha, Arun K.
Format:	Artikel
Sprache:	eng
Schlagworte:	cascade C−N and C−S/C−Se bond cooperative catalysis heterocycles Indoles Iodine LC−MS based reaction mechanism reduction-cyclization-chalcogenylation Regioselectivity Selenides Synthesis
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container_title	Advanced synthesis & catalysis
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creator	Lavekar, Aditya G. Equbal, Danish Saima Sinha, Arun K.
description	In this work, a new strategy to synthesize 3‐sulfenyl/selenyl indole is reported wherein LC−MS reveals a novel insight into synergistic cooperative effect of NaBH4‐I2 which allows cascade C−N and C−S/C−Se bond formations via reduction‐nucleophilic cyclization‐chalcogenylation, three steps in one‐pot, towards regioselective synthesis of diverse 3‐chalcogenyl indoles including 5‐bromo‐3‐[(3,4,5‐trimethoxyphenyl)thio]‐1H‐indole, a known lead anticancer compound, directly from 2‐amino‐phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition‐metal‐free condition.
doi_str_mv	10.1002/adsc.201701028
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subjects	cascade C−N and C−S/C−Se bond cooperative catalysis heterocycles Indoles Iodine LC−MS based reaction mechanism reduction-cyclization-chalcogenylation Regioselectivity Selenides Synthesis
title	Synergistic Cooperative Effect of Sodium borohydride‐Iodine Towards Cascade C−N and C−S/Se Bond Formation: One‐pot Regioselective Synthesis of 3‐Sulfenyl/selenyl Indoles and Mechanistic Insight
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