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Counter Ion Effect in Au/Ag-Catalyzed Chemoselective 6-endo-dig N‑ and O‑Cyclizations of Enyne–Urea System: Diversity-Oriented Synthesis of Annulated Indoles
A two-step protocol for the diversity-oriented synthesis of annulated indoles following MCR-post MCR modification concept is described. The reaction initially proceeds through the annulation of 2-(2,2-dibromovinyl)aniline, an isocyanate, and a terminal alkyne in a three-component tandem format via C...
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Published in: | Journal of organic chemistry 2013-09, Vol.78 (17), p.8624-8633 |
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container_end_page | 8633 |
container_issue | 17 |
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container_title | Journal of organic chemistry |
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creator | Gupta, Sahaj Koley, Dipankar Ravikumar, Krishnan Kundu, Bijoy |
description | A two-step protocol for the diversity-oriented synthesis of annulated indoles following MCR-post MCR modification concept is described. The reaction initially proceeds through the annulation of 2-(2,2-dibromovinyl)aniline, an isocyanate, and a terminal alkyne in a three-component tandem format via Cu/Pd-catalyzed cross coupling to afford N-1 and C-2 functionalized indole. In the subsequent step, the enyne–urea derivative undergoes chemo- and regioselective 6-endo cyclization to afford O-cyclized product in the presence of Au(I)/AgNO3 and N-cyclized product in the presence of Au(I)/AgOTf under a post-MCR modification step. A mechanistic investigation following a recent pioneering work on the silver effect in gold catalysis ( Shi X. J. Am. Chem. Soc. 2012, 134, 9012 ) explains the role of counterion on Au/Ag-catalyzed regiodivergent pathways. |
doi_str_mv | 10.1021/jo4013332 |
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The reaction initially proceeds through the annulation of 2-(2,2-dibromovinyl)aniline, an isocyanate, and a terminal alkyne in a three-component tandem format via Cu/Pd-catalyzed cross coupling to afford N-1 and C-2 functionalized indole. In the subsequent step, the enyne–urea derivative undergoes chemo- and regioselective 6-endo cyclization to afford O-cyclized product in the presence of Au(I)/AgNO3 and N-cyclized product in the presence of Au(I)/AgOTf under a post-MCR modification step. A mechanistic investigation following a recent pioneering work on the silver effect in gold catalysis ( Shi X. J. Am. Chem. 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Soc. 2012, 134, 9012 ) explains the role of counterion on Au/Ag-catalyzed regiodivergent pathways.</description><subject>Alkynes - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Gold - chemistry</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Molecular Structure</subject><subject>Silver - chemistry</subject><subject>Urea - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptkU1uFDEQhS0EIkNgwQWQN0iwMPH_dLMbNQOMFDELwrrlaVcnjrrtYLuROqtcAXEBFpyEo-QkeJiQFd7Y5freK5UeQs8ZfcMoZyeXQVImhOAP0IIpTomuqXyIFpRyTgTX4gg9SemSlqOUeoyOuKjquhQL9KsJk88Q8SZ4vO576DJ2Hq-mk9U5aUw2w3wNFjcXMIYEQ2m7b4A1AW8Dse4cf7q9-f77p_EWb8urmbvBXZvsgk849HjtZw-3Nz--RDD485wyjG_xu2IRk8sz2UYHZbotLZ8vILm_opX302D235syZYD0FD3qzZDg2d19jM7er8-aj-R0-2HTrE6JERXLRO8YBaGYrRitrQWmoWKKUqOlWapOA9-pTlaMWb6UBrjQVvadULLWy55zcYxeHWyvYvg6Qcrt6FIHw2A8hCm1TApayaVme_T1Ae1iSClC315FN5o4t4y2-0za-0wK--LOdtqNYO_JfyEU4OUBMF0quin6suR_jP4A_dyWew</recordid><startdate>20130906</startdate><enddate>20130906</enddate><creator>Gupta, Sahaj</creator><creator>Koley, Dipankar</creator><creator>Ravikumar, Krishnan</creator><creator>Kundu, Bijoy</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20130906</creationdate><title>Counter Ion Effect in Au/Ag-Catalyzed Chemoselective 6-endo-dig N‑ and O‑Cyclizations of Enyne–Urea System: Diversity-Oriented Synthesis of Annulated Indoles</title><author>Gupta, Sahaj ; Koley, Dipankar ; Ravikumar, Krishnan ; Kundu, Bijoy</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-6b10e351d8109dde16e81500a64a75c6e2b5c4811d274ae236d4fc354967f223</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>Alkynes - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Gold - chemistry</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Molecular Structure</topic><topic>Silver - chemistry</topic><topic>Urea - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gupta, Sahaj</creatorcontrib><creatorcontrib>Koley, Dipankar</creatorcontrib><creatorcontrib>Ravikumar, Krishnan</creatorcontrib><creatorcontrib>Kundu, Bijoy</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gupta, Sahaj</au><au>Koley, Dipankar</au><au>Ravikumar, Krishnan</au><au>Kundu, Bijoy</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Counter Ion Effect in Au/Ag-Catalyzed Chemoselective 6-endo-dig N‑ and O‑Cyclizations of Enyne–Urea System: Diversity-Oriented Synthesis of Annulated Indoles</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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source | American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list) |
subjects | Alkynes - chemistry Catalysis Cyclization Gold - chemistry Indoles - chemical synthesis Indoles - chemistry Molecular Structure Silver - chemistry Urea - chemistry |
title | Counter Ion Effect in Au/Ag-Catalyzed Chemoselective 6-endo-dig N‑ and O‑Cyclizations of Enyne–Urea System: Diversity-Oriented Synthesis of Annulated Indoles |
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