183677-72-7Relevant articles and documents
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.
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