73681-65-9Relevant articles and documents
Inter- and intra-molecular C-H borylation for the formation of PAHs containing triarylborane and indole units
Escande,Crossley,Cid,Cade,Vitorica-Yrezabal,Ingleson
supporting information, p. 17160 - 17167 (2016/11/13)
Inter-/intra-molecular electrophilic C-H borylation of C4-substituted indoles enables the formation of fused polycyclic aromatic structures containing triarylborane and N-heterocyclic units. These compounds are B-(C)n-N isosteres of carbocyclic PAHs that do not contain B-N bonds and comparison of one pair of BN/CC isosteres reveals that different resonance structures dominate. These compounds are highly sensitive to protodeboronation, of both the chloroborane intermediates and the mesityl protected products, which results in low isolated yields of the latter. Protodeboronation can be utilised productively for a C-H directed, C-H electrophilic borylation to make a previously unknown pinacol boronate ester by selective protodeboronation of the chloroborane intermediate. Intermolecular and double intramolecular electrophilic C-H borylation of a C4-substituted indole leads to a more highly fused structure containing two boracycles which represents a B-(C)n-N analogue of the unknown carbon isostere indeno[1,7ab]perylene.
Direct C-C bond construction from arylzinc reagents and aryl halides without external catalysts
Minami, Hiroki,Wang, Xuan,Wang, Chao,Uchiyama, Masanobu
supporting information, p. 7891 - 7894 (2014/01/06)
Direct cross-coupling between an arylzinc reagent and an aryl halide was accomplished without any external catalyst, enabling efficient and selective formation of the corresponding biaryl compound with broad functional group compatibility. Direct cross-coupling between a diarylzinc compound and an aryl iodide was accomplished without using any external catalyst. The reaction is efficient and selective, enabling formation of the corresponding biaryl compounds with broad functional group compatibility. The reaction is proposed to proceed by a thermally initiated single electron transfer (SET) route. Copyright