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膦取代的炔基硼酸酯和炔基三氟硼酸盐的合成、表征及反应

Synthesis, characterisation and reactions of phosphine-substituted alkynylboronates and alkynyltrifluoroborate salts.

作者信息

Vivat Jérôme F, Bachollet Sylvestre P J T, Adams Harry, Harrity Joseph P A

机构信息

Department of Chemistry, University of Sheffield, Sheffield S3 7HF, UK.

出版信息

Molecules. 2014 Dec 18;19(12):21324-34. doi: 10.3390/molecules191221324.

DOI:10.3390/molecules191221324
PMID:25529019
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6271442/
Abstract

The synthesis and structural characterisation of phosphine-substituted alkynylboronates is reported. A P(III)-centred alkynylboronate (2) was prepared that showed little evidence for the conjugation of the P-lone pair to the boron via the alkyne π-system, as judged by X-ray crystallography studies of 2 and a related P(V) compound, 3. In addition, corresponding alkynyltrifluoroborate salts were prepared that showed improved stability by comparison to their boronic ester counterparts. These salts undergo Pd-catalysed cross-coupling reactions with aryl halides.

摘要

报道了膦取代的炔基硼酸酯的合成及结构表征。制备了一种以P(III)为中心的炔基硼酸酯(2),通过对2和相关的P(V)化合物3进行X射线晶体学研究判断,几乎没有证据表明P孤对电子通过炔烃π体系与硼共轭。此外,制备了相应的炔基三氟硼酸盐,与它们的硼酸酯对应物相比,其稳定性有所提高。这些盐可与芳基卤化物发生钯催化的交叉偶联反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/b27f735d1bee/molecules-19-21324-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/dcb2c9085f23/molecules-19-21324-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/d947484371ca/molecules-19-21324-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/d15a06ca49b4/molecules-19-21324-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/4d6e9fdb181c/molecules-19-21324-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/d7c363ebb0e3/molecules-19-21324-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/4762990b196f/molecules-19-21324-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/7b40d7f6cbbf/molecules-19-21324-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/b27f735d1bee/molecules-19-21324-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/dcb2c9085f23/molecules-19-21324-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/d947484371ca/molecules-19-21324-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/d15a06ca49b4/molecules-19-21324-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/4d6e9fdb181c/molecules-19-21324-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/d7c363ebb0e3/molecules-19-21324-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/4762990b196f/molecules-19-21324-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/7b40d7f6cbbf/molecules-19-21324-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e8b5/6271442/b27f735d1bee/molecules-19-21324-g008.jpg

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