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Volumn 21, Issue 40, 2015, Pages 13930-13933

Organosulfide-Catalyzed Diboration of Terminal Alkynes under Light

Author keywords

alkynes; borylation; organocatalysis; photochemistry; sulfides

Indexed keywords

CATALYSIS; HEAVY METALS; HYDROCARBONS; MAGNETIC MOMENTS; PHOTOCHEMICAL REACTIONS; SULFUR COMPOUNDS;

EID: 84941763910     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201502425     Document Type: Article
Times cited : (64)

References (71)
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    • 1H NMR yields were always lower than the yields of isolated product, perhaps partly because the presence of a radical species in the mixture.
    • 1H NMR yields were always lower than the yields of isolated product, perhaps partly because the presence of a radical species in the mixture.
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    • The excess B2pin2 used can be recovered after the reaction. The formation of the byproduct 2 a by the addition of (PhS)2 to 1-octyne was effectively suppressed in the presence of an excess amount of B2pin2
    • The excess B2pin2 used can be recovered after the reaction. The formation of the byproduct 2 a by the addition of (PhS)2 to 1-octyne was effectively suppressed in the presence of an excess amount of B2pin2.
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    • A white precipitate was observed in methanol or acetonitrile, owing to the formation of a complex of B2pin2 with the solvent. When DMSO was used as a solvent, 1 a was obtained in 22 % yield along with some thiolation products (11 % yield).
    • A white precipitate was observed in methanol or acetonitrile, owing to the formation of a complex of B2pin2 with the solvent. When DMSO was used as a solvent, 1 a was obtained in 22 % yield along with some thiolation products (11 % yield).
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    • (PhS)2 has an absorption maxima at λmax=250 nm. It was assumed that (PhS)2 was first activated by light. The boryl-centered radical was then generated by an energy transfer from the activated (PhS)2
    • (PhS)2 has an absorption maxima at λmax=250 nm. It was assumed that (PhS)2 was first activated by light. The boryl-centered radical was then generated by an energy transfer from the activated (PhS)2.
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    • The exact structure of the radical has not yet been determined. However, it was clear that this is not a sulfide-centered radical judging from its g value. It should be the boryl-centered radical, which works as the key species during the reaction. For ESR of organosulfur radicals, see.
    • The exact structure of the radical has not yet been determined. However, it was clear that this is not a sulfide-centered radical judging from its g value. It should be the boryl-centered radical, which works as the key species during the reaction. For ESR of organosulfur radicals, see:, H. Taniguchi, J. Phys. Chem. 1984, 88, 6245-6250.
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    • To our knowledge, catalysis by a combination of (PhS)2 with light is unknown. For chalcogenide organocatalysts, see
    • To our knowledge, catalysis by a combination of (PhS)2 with light is unknown. For chalcogenide organocatalysts, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.