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• W2226255435 endingPage "4005" @default.
• W2226255435 startingPage "3995" @default.
• W2226255435 abstract "Abstract 2‐Unsubstituted N ‐alkyl‐1,3‐benzazaphospholes, diagonally P–C related to 2,3‐unsubstituted indoles, were successfully arylated by aryl iodides and bromides or alkylated by neopentyl iodide by heating in DMF in the presence of a catalytic amount of PdCl 2 or H 2 PtCl 6 and a suitable base. In contrast to the known 2‐arylations of indoles under these conditions, the reactions led to arylation in the 3‐position and proceeded via highly moisture‐sensitive intermediates to P ‐substituted 1,3‐benzazaphosphole P ‐oxides. Thus, we present a novel route for the direct P ‐substitution of aromatic σ 2 P‐heterocycles with electrophilic aryl/alkyl halides. Characteristic NMR spectroscopic data of the intermediates are consistent with –P(aryl)–C(Br/Cl)–N– species formed by metal‐mediated addition of the aryl halides at the P=C bond rather than by oxidative addition to ylidic intermediates. Benzazaphospholium salts, accessible by using triethyloxonium tetrafluoroborate at room temperature and also very sensitive to hydrolysis, display distinct NMR spectroscopic data. The structures of the products were elucidated by conclusive NMR spectroscopy and HRMS data and crystal‐structure analysis. Minor amounts of a bis(arylation) product could likewise be identified by crystal‐structure analysis." @default.
• W2226255435 created "2016-06-24" @default.
• W2226255435 creator A5025689362 @default.
• W2226255435 creator A5052284873 @default.
• W2226255435 creator A5058269346 @default.
• W2226255435 creator A5089476171 @default.
• W2226255435 date "2015-07-17" @default.
• W2226255435 modified "2023-10-10" @default.
• W2226255435 title "π‐Excess σ ² P=C–N–Heterocycles: Catalytic <i>P</i> ‐Arylation and Alkylation of <i>N</i> ‐Alkyl‐1,3‐benzazaphospholes and Isolation of <i>P</i> , <i>N</i> ‐Disubstituted Dihydrobenzaza­phosphole <i>P</i> ‐Oxides" @default.
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• W2226255435 doi "https://doi.org/10.1002/ejic.201500532" @default.
• W2226255435 hasPublicationYear "2015" @default.
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