93296-09-4Relevant articles and documents
Water-Soluble Phospholo[3,2-b]phosphole-P,P′-Dioxide-Based Fluorescent Dyes with High Photostability
Wang, Chenguang,Fukazawa, Aiko,Tanabe, Yoshiyuki,Inai, Naoto,Yokogawa, Daisuke,Yamaguchi, Shigehiro
, p. 1616 - 1624 (2018)
We recently reported that fluorescent dye PB430, which consisted of a 2-phenyl-substituted benzophosphole P-oxide skeleton that was reinforced by a methylene bridge, showed pronounced photostability and, thus, high utility for applications in super-resolution stimulated emission depletion (STED) microscopy. Herein, we replaced the methylene bridge with another P=O group to 1) investigate the role of the bridging moieties; and 2) further modulate the fluorescence properties of this skeleton. We synthesized a series of phospholo[3,2-b]phosphole-based dyes—trans-PO-PB430, cis-PO-PB430, and trans-PO-PB460—all of which showed sufficient water solubility. Moreover, trans-PO-PB430 and trans-PO-PB460 exhibited intense green and orange fluorescence, respectively, and a high photostability that was comparable to that of PB430. In contrast, cis-PO-PB430 underwent rapid photobleaching upon continuous photoirradiation, which demonstrated the importance of steric shielding of the polycyclic skeleton by the substituents on the bridging moieties. The fluorescence properties of these dyes were insensitive to concentration, pH value, and polarity changes of the environment in solution. In addition, even in the solid state, these dyes showed strong green to orange emissions. These results demonstrate the potential utility of trans-PO-PB430 and trans-PO-PB460 as highly photostable fluorescent dyes.
Enantiomerically Enriched α-Borylzinc Reagents by Nickel-Catalyzed Carbozincation of Vinylboronic Esters
Chen, Jingjia,Hu, Weipeng,Jin, Jing,Lovinger, Gabriel J.,Morken, James P.,Zhang, Chenlong
supporting information, p. 14189 - 14195 (2021/09/11)
In this paper is described a synthesis of enantiomerically enriched, configurationally stable organozinc reagents by catalytic enantioselective carbozincation of a vinylboronic ester. This process furnishes enantiomerically enriched α-borylzinc intermediates that are shown to undergo stereospecific reactions, producing enantioenriched secondary boronic ester products. The properties of the intermediate α-borylzinc reagent are probed and the synthetic utility of the products is demonstrated by application to the synthesis of (-)-aphanorphine and (-)-enterolactone.
Ni-Catalyzed C(sp3)–O Arylation of α-Hydroxy Esters
Monteith, John J.,Rousseaux, Sophie A. L.
supporting information, p. 9485 - 9489 (2021/12/09)
A Negishi cross-coupling of α-hydroxy ester derivatives and arylzinc reagents has been developed. This reaction tolerates both primary and secondary C(sp3)–O alcohol precursors and achieves efficient cross-coupling under Ni catalysis without the need for added external metal reductant, photocatalyst, or additives. The arylation of readily accessible C(sp3)–O electrophiles in this operationally simple, rapid, and mild reaction provides a complementary way of accessing desirable α-aryl ester products.
