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Visible-Light-Induced Chemoselective Deboronative Alkynylation under Biomolecule-Compatible Conditions
Alternative Title可见光引发的化学选择的脱硼炔基化反应与生物大分子相容
Huang HC(黄汉初); Zhang GJ(张国晋); Gong L(宫莉); Zhang SY(张帅琰); Chen YY(陈以昀)
2014
Source PublicationJ. Am. Chem. Soc.
Volume136Issue:6Pages:2280-2283
AbstractHere, we report a visible-light-induced deboronative alkynylation reaction, which is redox-neutral and works with primary, secondary and tertiary alkyl trifluoroborates or boronic acids to generate aryl, alkyl and silyl substituted alkynes. This reaction is highly chemoselective and performs well on substrates containing alkenes, alkynes, aldehydes, ketones, esters, nitriles, azides, aryl halides, alkyl halides, alcohols, and indoles, with no detectable occurrence of side reactions. The mechanism of this novel C(sp(3))-C(sp) bond coupling reaction was investigated by luminescence quenching, radical trapping, on-off light, and C-13-isotopic-labeling experiments. This reaction can be performed in neutral aqueous conditions, and it is compatible with amino acids, nucleosides, oligosaccharides, nucleic acids, proteins, and cell lysates.
Subject Area生命有机化学
DOI10.1021/ja413208y
URL查看原文
Indexed BySCI
Language英语
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Cited Times:126[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/38933
Collection生命有机化学国家重点实验室
Corresponding AuthorChen YY(陈以昀)
Affiliation中科院上海有机化学研究所
Recommended Citation
GB/T 7714
Huang HC,Zhang GJ,Gong L,et al. Visible-Light-Induced Chemoselective Deboronative Alkynylation under Biomolecule-Compatible Conditions[J]. J. Am. Chem. Soc.,2014,136(6):2280-2283.
APA 黄汉初,张国晋,宫莉,张帅琰,&陈以昀.(2014).Visible-Light-Induced Chemoselective Deboronative Alkynylation under Biomolecule-Compatible Conditions.J. Am. Chem. Soc.,136(6),2280-2283.
MLA 黄汉初,et al."Visible-Light-Induced Chemoselective Deboronative Alkynylation under Biomolecule-Compatible Conditions".J. Am. Chem. Soc. 136.6(2014):2280-2283.
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