183677-72-7Relevant academic research and scientific papers
Alkynyl Moiety for Triggering 1,2-Metallate Shifts: Enantiospecific sp2–sp3 Coupling of Boronic Esters with p-Arylacetylenes
Ganesh, Venkataraman,Odachowski, Marcin,Aggarwal, Varinder K.
, p. 9752 - 9756 (2017/08/08)
The enantiospecific coupling of secondary and tertiary boronic esters to aromatics has been investigated. Using p-lithiated phenylacetylenes and a range of boronic esters coupling has been achieved by the addition of N-bromosuccinimide (NBS). The alkyne functionality of the intermediate boronate complex reacts with NBS triggering the 1,2-migration of the group on boron to carbon giving a dearomatized bromoallene intermediate. At this point elimination and rearomatization occurs with neopentyl boronic esters, giving the coupled products. However, using pinacol boronic esters, the boron moiety migrates to the adjacent carbon resulting in formation of ortho boron-incorporated coupled products. The synthetic utility of the boron incorporated product has been demonstrated by orthogonal transformation of both the alkyne and boronic ester functionalities.
Design and synthesis of fluorescent 7-deazaadenosine nucleosides containing π-extended diarylacetylene motifs
De Ornellas, Sara,Slattery, John M.,Edkins, Robert M.,Beeby, Andrew,Baumann, Christoph G.,Fairlamb, Ian J. S.
supporting information, p. 68 - 72 (2015/02/02)
C-modified 7-deazaadenosines containing a diphenylacetylene moiety have been synthesised using cross-coupling approaches. The C-modified nucleosides exhibit remarkable fluorescence properties, including high quantum yields. Solvatochromic studies show a n
Effect of extended conjugation with a phenylethynyl group on the fluorescence properties of water-soluble arylboronic acids
Zheng, Shi-Long,Lin, Na,Reid, Suazette,Wang, Binghe
, p. 5427 - 5436 (2008/01/07)
Boronic acids that change fluorescence properties upon sugar binding are very important reporter units for the development of small molecule lectin mimics (boronolectins). Aimed at developing long wavelength fluorescent boronic acid reporter compounds, we
Microwave-assisted synthesis of ethynylarylboronates for the construction of boronic acid-based fluorescent sensors for carbohydrates
Zheng, Shi-Long,Reid, Suazette,Lin, Na,Wang, Binghe
, p. 2331 - 2335 (2007/10/03)
A reliable and operationally simple procedure for the synthesis of 2,2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 was developed. The key step is microwave-facilitated selective formation of 2,2-dimethylpropane-1,3-diyl trimethylsilylethynylaryl boro
