Synthesis of Sb-chiral organoantimony compounds having intramolecular Sb⋯N interaction and their separation into optically pure compounds via ortho-palladated benzylamine complexes

An Organobismuth Compound that Exhibits Selective Cytotoxicity to Vascular Endothelial Cells in Vitro

“…Compounds 05, 06, 28, and 29 were prepared by the reaction of SbCl 3 were synthesized as described previously. [8][9][10][11][12][13][14][15][16][17][18][19][20][21] The lactate dehydrogenase (LDH) kit, bismuth nitrate, and other reagents were from Wako Pure Chemical Industries (Osaka, Japan). Cytotoxicity Assay ---Vascular endothelial cells, vascular smooth muscle cells, LLC-PK 1 cells, and IMR-90 cells were each cultured in DMEM supplemented with 10% FBS in 24-well culture plates at 37°C in a humid atmosphere of 5% CO 2 in air until confluence.…”

Neutral organoantimony(III) and organobismuth(III) ligands as acceptors in transition metal complexes – Role of substituents and co-ligands

“…13 , 14 Complexation with transition metal centres has been used to help characterise these organostibines, and can be used to enantiomerically resolve Sb-chiral species. 15 In such complexes the 'hypervalent'…”

Synthesis, Structure and Applications of Hypervalent Organoantimony Compounds Having Intramolecular E→Sb (E = N, O, S) Coordinations

“…Kurita and co-workers recently reported the synthesis of Sbchiral triarylstibines (12a-c), having intramolecular N Sb coordinations generated by stepwise nucleophilic displacement of the ethynyl groups on diethynylstibanes with Grignard and organolithium reagents (Scheme 4) [19]. Single-crystal XRD analysis of 12b revealed that there is intramolecular interaction between the antimony and nitrogen atom, and the N-Sb distance in 12b is 2.886(5) Å.…”

“…They can be prepared by methods such as redistribution, halogen exchange, and salt elimination of organometallic reagents with antimony trihalides. In 1997, Carmalt et al reported the syntheses and structures of diarylantimony(III) monochlorides 18, 19 and monoarylantimony dichloride 20 [23]. The compounds (18)(19)(20) were prepared via the salt elimination reaction of ArLi (Ar = 2-(Me 2 NCH 2 )C 6 H 4 , or 8-(Me 2 N)C 10 H 6 ) [56].…”

“…Recent development shows that with the avoidance of bulky ligands such as (Me 3 Si) 2 CH [14], and 2,6-Mes 2 C 6 H 3 [15], the use of aryl ligands with one or two pendant arms (e.g. 2-(Me 2 NCH 2 )C 6 H 4 [16][17][18][19], 2,6-(Me 2 NCH 2 ) 2 C 6 H 3 [20,21], and 2,6-(ROCH 2 ) 2 C 6 H 3 (R = Me, t-Bu [22]), as well as those ortho-substituted with CH 2 NMe 2 [23,24]) or analogous ligands such as RN(CH 2 C 6 H 4 ) 2 (R = Me, t-Bu, cyclohexyl, Ph [25]) and S(CH 2 C 6 H 4 ) 2 [26] is a common strategy to generate stable organoantimony compounds. In all cases, intramolecular N, O, S Sb coordinations were observed in solution and/or solid state.…”