钽联吡啶化合物与腈、异(硫)氰酸酯和碳二亚胺的反应性研究

doi:10.6023/A26070231

摘要/Abstract

钽联吡啶化合物(2,6-ⁱPr₂C₆H₃O)₃Ta(bipy) (1)对有机不饱和小分子表现出了丰富的反应性. 例如, PhCN中的C≡N三键可以被化合物1还原, 进而选择性地与联吡啶基团的C6/C6'发生C—C偶联并进一步发生1,5-氢迁移, 生成钽亚胺化合物(2,6-ⁱPr₂C₆H₃O)₃Ta(=NCHPh)(C₁₀H₇N₂) (2); 2可继续通过1,5-氢迁移生成二氮杂钽杂环戊烯化合物(2,6-ⁱPr₂C₆H₃O)₃Ta(N₂C₁₀H₇C(Ph)NH) (3). 同样, p-MeC₆H₄CH₂CN、MeCN、CyCN和^tBuCN均可与1发生类似的反应, 生成化合物(2,6-ⁱPr₂C₆H₃O)₃Ta(=NCH(R))(C₁₀H₇N₂) (R=p-MeC₆H₄CH₂ (4), Me (5), Cy (6), ^tBu (7)); 除7之外, 化合物4~6可进一步转化为1,5-氢迁移产物(2,6-ⁱPr₂C₆H₃O)₃Ta(N₂C₁₀H₇C(R)NH) (R=p-MeC₆H₄CH₂ (8), Me (9), Cy (10)). 另外, 异(硫)氰酸酯可以选择性地与化合物1中联吡啶基团的C2/C2'发生C—C偶联, 生成插入产物(2,6-ⁱPr₂C₆H₃O)₃- Ta(bipy)(PhNCS) (11), (2,6-ⁱPr₂C₆H₃O)₃Ta(bipy)(CyNCO) (12)和(2,6-ⁱPr₂C₆H₃O)₃Ta(bipy)(^tBuNCO) (13); 化合物1还可作为Ta(III)合成子与碳二亚胺发生双电子转移反应, 生成中性联吡啶配位的钽亚胺化合物(2,6-ⁱPr₂C₆H₃O)₃Ta(=NPh)- (bipy⁰) (R=Ph (14), ⁱPr (15), Cy (16)).

关键词: 反应性, 有机钽化合物, 联吡啶配合物, 小分子活化, 合成

Complexes of main group metals, lanthanides and actinides bearing reduced bipy ligand have garnered considerable attention and demonstrated notable potential in small-molecule activation. Nevertheless, the detailed reactivity studies on 2,2'-bipyridine-derived tantalum complexes remain largely unexplored. In this work, the divergent reactivity of a direduced bipyridyl tantalum complex (2,6-ⁱPr₂C₆H₃O)₃Ta(bipy) (1) toward small molecules bearing highly unsaturated functional groups is explored. For instance, when treatment of complex 1 with 1.0 equiv. of benzonitrile (PhCN) at room temperature, the C≡N bond in PhCN can insert into the bipy moiety of complex 1 through the reduction of C≡N bond followed by C—C coupling occurring at C6 or C6' of bipy in 1 and 1,5-H migration, forming the imido complex (2,6-ⁱPr₂C₆H₃O)₃Ta-(=NCHPh)(C₁₀H₇N₂) (2), which can further undergo 1,5-H migration at 100 ℃ to yield the bis-amido complex (2,6-ⁱPr₂C₆H₃O)₃Ta(N₂C₁₀H₇C(Ph)NH) (3). The aliphatic nitriles, including p-tolylacetonitrile (p-MeC₆H₄CH₂CN), acetonitrile (MeCN), cyclohexanecarbonitrile (CyCN) and pivalonitrile (^tBuCN) with primary, secondary, tertiary and quaternary carbons at the α-position of cyano group, respectively, react with 1 to form the analogous imido products (2,6-ⁱPr₂C₆H₃O)₃Ta(=NCH(R))(C₁₀H₇N₂) (R=p-MeC₆H₄CH₂ (4), Me (5), Cy (6) and ^tBu (7)). Among which, complexes 4-6 can also transform via 1,5-H migration into bis-amido complexes (2,6-ⁱPr₂C₆H₃O)₃Ta(N₂C₁₀H₇C(p-MeC₆H₄CH₂)NH) (8), (2,6-ⁱPr₂C₆H₃O)₃Ta(N₂C₁₀H₇C(Me)NH) (9) and (2,6-ⁱPr₂C₆H₃O)₃Ta(N₂C₁₀H₇C(Cy)NH) (10), respectively, whereas, complex 7 remains inert even when its toluene solution was heated at 120 ℃ for one week. Furthermore, phenyl isothiocyanate (PhNCS) and alkyl isocyanates (CyNCO and ^tBuNCO) can regioselectively couple with C2 or C2' of bipy moiety in 1 to form the insertion products (2,6-ⁱPr₂C₆H₃O)₃Ta(bipy)(PhNCS) (11), (2,6-ⁱPr₂C₆H₃O)₃Ta(bipy)(CyNCO) (12), and (2,6-ⁱPr₂C₆H₃O)₃Ta(bipy)(^tBuNCO) (13), respectively. During this process, the C=S and C=O bonds in iso(thio)cyanates are reduced, whereas the N=C double bonds remain intact, as confirmed by X-ray diffraction analysis. Conversely, 1 acts as a low valent Ta(III) synthon for (2,6-ⁱPr₂C₆H₃O)₃Ta(III)(bipy) when reacted with organic carbodiimides (RN=C=NR) (R=Ph, ⁱPr and Cy), yielding the neutral bipy coordinated tantalum imido complexes (2,6-ⁱPr₂C₆H₃O)₃Ta(=NR)(bipy⁰) (R=Ph (14), ⁱPr (15) and Cy (16)) via two-electron redox process.

Key words: reactivity, organotantalum, bipyridyl complex, small molecule activation, synthesis

引用此文

张磊, 张萍, 张艳峰. 钽联吡啶化合物与腈、异(硫)氰酸酯和碳二亚胺的反应性研究[J]. 化学学报, 2026, 84(10): 1641-1648.

Lei Zhang, Ping Zhang, Yanfeng Zhang. Reactivity of a Bipyridyl Tantalum Complex toward Nitriles, Iso(thio)cyanates and Carbodiimides[J]. Acta Chimica Sinica, 2026, 84(10): 1641-1648.

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图/表 6

图式1. 化合物2~10的合成

Scheme 1. Syntheses of complexes 2~10

图1. 化合物2(上)和3(下)的分子结构(椭球率为30%, 与氧原子相的2,6-iPr2C6H3基团以线框形式绘制). 部分键长(nm): 2, Ta—N(1) 0.2386(4), Ta—N(2) 0.2265(4), Ta—N(3) 0.1798(4), C(41)—C(42) 0.1471(9), C(46)—C(47) 0.1517(8), N(3)—C(47) 0.1464(7); 3, Ta—N(1) 0.2254(2), Ta—N(2) 0.2140(2), Ta—N(3) 0.1996(2), C(41)—C(42) 0.1455(5), C(46)—C(47) 0.1359(4), N(3)—C(47) 0.1396(4)

Figure 1. Molecular structures of 2 (top) and 3 (bottom) (thermal ellipsoids drawn at the 30% probability level, 2,6-iPr2C6H3 moieties attached to O atoms drawn in a wireframe for clarity). Selected bond lengths (nm): 2, Ta—N(1) 0.2386(4), Ta—N(2) 0.2265(4), Ta—N(3) 0.1798(4), C(41)—C(42) 0.1471(9), C(46)—C(47) 0.1517(8), N(3)—C(47) 0.1464(7); 3, Ta—N(1) 0.2254(2), Ta—N(2) 0.2140(2), Ta—N(3) 0.1996(2), C(41)—C(42) 0.1455(5), C(46)—C(47) 0.1359(4), N(3)—C(47) 0.1396(4)

图式2. 化合物11~13的合成

Scheme 2. Syntheses of complexes 11~13

图2. 化合物11(上)和12(下)的分子结构(椭球率为30%, 与氧原子相连的2,6-iPr2C6H3基团以线框形式绘制). 部分键长(nm): 11, Ta—N(1) 0.2283(5), Ta—N(2) 0.2062(5), Ta—S(1) 0.25215(17), C(41)—C(42) 0.1525(11), C(42)—C(47) 0.1564(11), N(3)—C(47) 0.1276(9), C(47)—S(1) 0.1744(8); 12, Ta—N(1) 0.2316(2), Ta—N(2) 0.2065(2), Ta—O(4) 0.20093(15), C(41)—C(42) 0.1536(4), C(42)—C(47) 0.1536(3), N(3)—C(47) 0.1258(3), C(47)—O(4) 0.1338(3)

Figure 2. Molecular structures of 11 (top) and 12 (bottom) (thermal ellipsoids drawn at the 30% probability level, 2,6-iPr2C6H3 moieties attached to O atoms drawn in a wireframe for clarity). Selected bond lengths (nm): 11, Ta—N(1) 0.2283(5), Ta—N(2) 0.2062(5), Ta—S(1) 0.25215(17), C(41)—C(42) 0.1525(11), C(42)—C(47) 0.1564(11), N(3)—C(47) 0.1276(9), C(47)—S(1) 0.1744(8); 12, Ta—N(1) 0.2316(2), Ta—N(2) 0.2065(2), Ta—O(4) 0.20093(15), C(41)—C(42) 0.1536(4), C(42)—C(47) 0.1536(3), N(3)—C(47) 0.1258(3), C(47)—O(4) 0.1338(3)

图式3. 化合物14~16的合成

Scheme 3. Syntheses of complexes 14~16

图3. 化合物15(上)和16(下)的分子结构(椭球率为30%, 与氧原子相连的2,6-iPr2C6H3基团以线框形式绘制). 部分键长(nm)和键角(°): 15, Ta—N(1) 0.24290(19), Ta—N(2) 0.23117(19), Ta—N(3) 0.1777(2), C(41)—C(42) 0.1479(4), Ta(1)—N(3)—C(47) 171.11(18); 16, Ta—N(1) 0.24219(18), Ta—N(2) 0.23032(17), Ta—N(3) 0.17773(18), C(41)—C(42) 0.1479(3), Ta(1)—N(3)—C(47) 176.20(15)

Figure 3. Molecular structures of 15 (top) and 16 (bottom) (thermal ellipsoids drawn at the 30% probability level, 2,6-iPr2C6H3 moieties attached to O atoms drawn in a wireframe for clarity). Selected bond lengths (nm) and angles (deg): 15, Ta—N(1) 0.24290(19), Ta—N(2) 0.23117(19), Ta—N(3) 0.1777(2), C(41)—C(42) 0.1479(4), Ta(1)—N(3)—C(47) 171.11(18); 16, Ta—N(1) 0.24219(18), Ta—N(2) 0.23032(17), Ta—N(3) 0.17773(18), C(41)—C(42) 0.1479(3), Ta(1)—N(3)—C(47) 176.20(15)

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