Matches in SemOpenAlex for { <https://semopenalex.org/work/W2950199254> ?p ?o ?g. }
- W2950199254 endingPage "4041" @default.
- W2950199254 startingPage "4031" @default.
- W2950199254 abstract "A detailed study of the scope of a new Pd-catalyzed synthesis of indoles from 1,2-dihaloarenes and o-halobenzene sulfonates and imines is described. The cascade reaction comprises an imine α-arylation followed by an intramolecular C−N bond-forming reaction promoted by the same Pd catalyst. The reaction with 1,2-dibromobenzene shows wide scope and allows the introduction of aryl, alkyl, and vinyl substituents at different positions of the five-membered ring of the indole. The regioselective synthesis of indoles substituted in the six-membered ring can be carried out by employing o-dihalobenzene derivatives with two different halogens, taking advantage of the different reactivities of I, Br, and Cl in oxidative addition reactions. This paper also introduces a method for the efficient cleavage of the N-t-butyl group, thus allowing for the preparation of N−H indoles through the same methodology. Finally, the reaction with o-halosulfonates has been studied. The best substrates are o-chlorononaflates, which lead to indoles in very high yield. The reaction is particularly appropriate for the synthesis of the challenging 6-substituted indoles. In view of the availability of o-chlorophenols, which are direct precursors of the chlorononaflates, this reaction represents an efficient entry into indoles substituted in the six-membered ring. The concept is illustrated by the preparation of a 4,6-disubstituted indole from naturally occurring anethole." @default.
- W2950199254 created "2019-06-27" @default.
- W2950199254 creator A5026315573 @default.
- W2950199254 creator A5053394574 @default.
- W2950199254 creator A5070219978 @default.
- W2950199254 creator A5078115222 @default.
- W2950199254 date "2009-02-26" @default.
- W2950199254 modified "2023-10-16" @default.
- W2950199254 title "Modular Synthesis of Indoles from Imines and <i>o</i>-Dihaloarenes or <i>o</i>-Chlorosulfonates by a Pd-Catalyzed Cascade Process" @default.
- W2950199254 cites W1557012298 @default.
- W2950199254 cites W1963791018 @default.
- W2950199254 cites W1966889781 @default.
- W2950199254 cites W1971643970 @default.
- W2950199254 cites W1979844089 @default.
- W2950199254 cites W1981417125 @default.
- W2950199254 cites W1984675434 @default.
- W2950199254 cites W1990258624 @default.
- W2950199254 cites W1990841567 @default.
- W2950199254 cites W1992043781 @default.
- W2950199254 cites W1992514547 @default.
- W2950199254 cites W2001614462 @default.
- W2950199254 cites W2002011964 @default.
- W2950199254 cites W2003857865 @default.
- W2950199254 cites W2008455207 @default.
- W2950199254 cites W2010278102 @default.
- W2950199254 cites W2018241366 @default.
- W2950199254 cites W2020419388 @default.
- W2950199254 cites W2024188074 @default.
- W2950199254 cites W2030248308 @default.
- W2950199254 cites W2031530240 @default.
- W2950199254 cites W2035265176 @default.
- W2950199254 cites W2040280837 @default.
- W2950199254 cites W2050331580 @default.
- W2950199254 cites W2052341221 @default.
- W2950199254 cites W2053036921 @default.
- W2950199254 cites W2053300772 @default.
- W2950199254 cites W2056465156 @default.
- W2950199254 cites W2056650671 @default.
- W2950199254 cites W2059664977 @default.
- W2950199254 cites W2070050023 @default.
- W2950199254 cites W2078526734 @default.
- W2950199254 cites W2090748242 @default.
- W2950199254 cites W2095596091 @default.
- W2950199254 cites W2101615823 @default.
- W2950199254 cites W2102408260 @default.
- W2950199254 cites W2103949778 @default.
- W2950199254 cites W2110687934 @default.
- W2950199254 cites W2113147745 @default.
- W2950199254 cites W2116919923 @default.
- W2950199254 cites W2119273253 @default.
- W2950199254 cites W2121573173 @default.
- W2950199254 cites W2124906740 @default.
- W2950199254 cites W2130106491 @default.
- W2950199254 cites W2131933593 @default.
- W2950199254 cites W2150805674 @default.
- W2950199254 cites W2151320294 @default.
- W2950199254 cites W2160889905 @default.
- W2950199254 cites W2161226035 @default.
- W2950199254 cites W2162707187 @default.
- W2950199254 cites W2164971329 @default.
- W2950199254 cites W2171550088 @default.
- W2950199254 cites W2179162529 @default.
- W2950199254 cites W2179673921 @default.
- W2950199254 cites W2180941630 @default.
- W2950199254 cites W2332246939 @default.
- W2950199254 cites W2882236489 @default.
- W2950199254 cites W2949068014 @default.
- W2950199254 cites W2949610586 @default.
- W2950199254 cites W2949694767 @default.
- W2950199254 cites W2951087586 @default.
- W2950199254 cites W2951559867 @default.
- W2950199254 cites W2952096981 @default.
- W2950199254 cites W2952491462 @default.
- W2950199254 cites W2952558059 @default.
- W2950199254 cites W2952970524 @default.
- W2950199254 cites W2953005465 @default.
- W2950199254 doi "https://doi.org/10.1021/ja808652a" @default.
- W2950199254 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/19245199" @default.
- W2950199254 hasPublicationYear "2009" @default.
- W2950199254 type Work @default.
- W2950199254 sameAs 2950199254 @default.
- W2950199254 citedByCount "150" @default.
- W2950199254 countsByYear W29501992542012 @default.
- W2950199254 countsByYear W29501992542013 @default.
- W2950199254 countsByYear W29501992542014 @default.
- W2950199254 countsByYear W29501992542015 @default.
- W2950199254 countsByYear W29501992542016 @default.
- W2950199254 countsByYear W29501992542017 @default.
- W2950199254 countsByYear W29501992542018 @default.
- W2950199254 countsByYear W29501992542019 @default.
- W2950199254 countsByYear W29501992542020 @default.
- W2950199254 countsByYear W29501992542021 @default.
- W2950199254 countsByYear W29501992542022 @default.
- W2950199254 countsByYear W29501992542023 @default.
- W2950199254 crossrefType "journal-article" @default.
- W2950199254 hasAuthorship W2950199254A5026315573 @default.
- W2950199254 hasAuthorship W2950199254A5053394574 @default.
- W2950199254 hasAuthorship W2950199254A5070219978 @default.