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Volumn 50, Issue 2, 2011, Pages 511-514

Direct synthesis of water-tolerant alkyl indium reagents and their application in palladium-catalyzed couplings with aryl halides

Author keywords

cross coupling; indium; organoindium reagents; palladium; synthesis design

Indexed keywords

ALKYL HALIDES; ARYL HALIDES; CATALYZED COUPLING; CROSS-COUPLINGS; DIRECT SYNTHESIS; N ,N-DIMETHYLACETAMIDE; ORGANIC SYNTHESIS; ORGANOINDIUM REAGENTS; SYNTHESIS DESIGN; SYNTHETIC UTILITY; TERT-BUTYLDIMETHYLSILYL;

EID: 78650915605     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005798     Document Type: Article
Times cited : (46)

References (81)
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    • 3In or other types of organoindium reagents with various electrophiles (such as aryl halide, acid chloride, benzyl halide, alkenyl halide), see
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    • Note
    • 1H-NMR spectra is approximately 1:1 (see the Supporting Information, page-S15). Furthermore, it was interesting to find that the alkyl indium reagent 2 a could decompose when THF was completely removed under reduced pressure or when it was purified by silica-gel column chromatography. Therefore, the presence of THF might play an important role in the stabilization of the alkyl indium reagent 2 a by coordinating with the indium center. Thus, the following structure was proposed for the alkyl indium reagent 2 a. For related crystal structures of organoindium reagents with a halide bridge and five-coordinated indium center, see
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    • Also see reference-[13c] for a similar allylic indium species, which was reported to be stabilized by the coordination of THF/pathalan with the indium center. In addition, the authors stated that removal of reaction solvents (THF and acetonitrile) may lead to the decomposition of the allylic indium species.
    • M. Yasuda, K. Kiyokawa, K. Osaki, A. Baba, Organometallics 2009, 28, 132. Also see reference-[13c] for a similar allylic indium species, which was reported to be stabilized by the coordination of THF/pathalan with the indium center. In addition, the authors stated that removal of reaction solvents (THF and acetonitrile) may lead to the decomposition of the allylic indium species.
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    • 2O was used as reaction additive (Table-1, entry-10) also proved that the alkyl indium reagent was not sensitive to water.
    • 2O was used as reaction additive (Table-1, entry-10) also proved that the alkyl indium reagent was not sensitive to water.
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    • note
    • The following solvents were screened for the conversion of 1-(2-bromoethyl)benzene to the corresponding alkyl indium reagent: THF, 65 °C, 24-h, <5 % yield; 1,4-dioxane, 100 °C, 24-h, 38 % yield; DMA, 100 °C, 24-h, >90 % yield; DMF, 100 °C, 24-h, >90 % yield. Considering that the subsequent palladium-catalyzed coupling reaction should be carried out in DMA, this was chosen as reaction solvent for the formation of the alkyl indium reagent from alkyl bromide.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.