34708-55-9Relevant academic research and scientific papers
Compound containing carbon-silicon bond and application thereof
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Paragraph 0252-0256, (2020/09/08)
The invention discloses a compound containing a carbon-silicon bond and application of the compound in construction of the carbon-carbon bond. The invention provides an application of a compound containing the carbon-silicon bond as shown in a formula I or a formula I' in a chemical reaction for constructing the carbon-carbon bond, wherein one carbon in the carbon-carbon bond is from carbon connected with silicon in the compound containing the carbon-silicon bond. According to the preparation method, the compound containing the carbon-silicon bond is used for providing a carbon free radical, and the carbon free radical can directly react with carbon provided in another molecule under a mild condition to construct the carbon-carbon bond; the preparation method is wider in substrate application range, is suitable for functional group activated C and carbon free radical substrates, and is also suitable for unactivated C-H bond substrates.
Catalytic asymmetric [2+2] cycloaddition between quinones and fulvenes and a subsequent stereoselective isomerization to 2,3-dihydrobenzofurans
Zheng, Haifeng,Xu, Chaoran,Wang, Yan,Kang, Tengfei,Liu, Xiaohua,Lin, Lili,Feng, Xiaoming
supporting information, p. 6585 - 6588 (2017/07/10)
The catalytic enantioselective [2+2] cycloaddition between quinones and fulvenes was achieved, for the first time, by the use of a chiral copper(ii) complex catalyst. The transformation afforded a series of enantiomerically enriched [6,4,5]-tricyclic cyclobutane derivatives in good yields with excellent regio- and stereoselectivities. Furthermore, the [2+2] adducts could be easily converted into formal [3+2] adducts efficiently and stereoselectively.
Visible-light-induced chemoselective deboronative alkynylation under biomolecule-compatible conditions
Huang, Hanchu,Zhang, Guojin,Gong, Li,Zhang, Shuaiyan,Chen, Yiyun
supporting information, p. 2280 - 2283 (2014/03/21)
Here, 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(sp3)-C(sp) bond coupling reaction was investigated by luminescence quenching, radical trapping, on-off light, and 13C-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.
Practical C-H functionalization of quinones with boronic acids
Fujiwara, Yuta,Domingo, Victoriano,Seiple, Ian B.,Gianatassio, Ryan,Del Bel, Matthew,Baran, Phil S.
supporting information; experimental part, p. 3292 - 3295 (2011/05/03)
A direct functionalization of a variety of quinones with several boronic acids has been developed. This scalable reaction proceeds readily at room temperature in an open flask using inexpensive reagents: catalytic silver(I) nitrate in the presence of a persulfate co-oxidant. The scope with respect to quinones is broad, with a variety of alkyl- and arylboronic acids undergoing efficient cross-coupling. The mechanism is presumed to proceed through a nucleophilic radical addition to the quinone with in situ reoxidation of the resulting dihydroquinone. This method has been applied to complex substrates, including a steroid derivative and a farnesyl natural product.
