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From Quaternary Carbon to Tertiary C(sp3)–Si and C(sp3)–Ge Bonds: Decyanative Coupling of Malononitriles with Chlorosilanes and Chlorogermanes Enabled by Ni/Ti Dual Catalysis
Journal of the American Chemical Society ( IF 15.0 ) Pub Date : 2024-05-13 , DOI: 10.1021/jacs.4c04495
Zi-Hao Chen 1 , Yu-Qing Zheng 1 , Hong-Gui Huang 1 , Ke-Hao Wang 1 , Jun-Lin Gong 1 , Wen-Bo Liu 1, 2
Affiliation  

Transition-metal-catalyzed C–Si/Ge cross-coupling offers promising avenues for the synthesis of organosilanes/organogermanes, yet it is fraught with long-standing challenges. A Ni/Ti-catalyzed strategy is reported here, allowing the use of disubstituted malononitriles as tertiary C(sp3) coupling partners to couple with chlorosilanes and chlorogermanes, respectively. This method enables the catalytic cleavage of the C(sp3)–CN bond of the quaternary carbon followed by the formation of C(sp3)–Si/C(sp3)–Ge bonds from ubiquitously available starting materials. The efficiency and generality are showcased by a broad scope for both of the coupling partners, therefore holding the potential to synthesize structurally diverse quaternary organosilanes and organogermanes that were difficult to access previously.

中文翻译:


从季碳到叔 C(sp3)–Si 和 C(sp3)–Ge 键:Ni/Ti 双催化下丙二腈与氯硅烷和氯锗烷的脱氰偶联



过渡金属催化的 C-Si/Ge 交叉偶联为有机硅烷/有机锗烷的合成提供了有前景的途径,但也充满了长期存在的挑战。本文报道了一种 Ni/Ti 催化策略,允许使用二取代丙二腈作为叔 C(sp 3 ) 偶联配偶体,分别与氯硅烷和氯锗烷偶联。该方法能够催化裂解季碳的 C(sp 3 )–CN 键,然后形成 C(sp 3 )–Si/C(sp 3 )–Ge 键来自普遍可用的起始材料。两种偶联伙伴的广泛范围展示了效率和通用性,因此具有合成以前难以获得的结构多样的季有机硅烷和有机锗烷的潜力。
更新日期:2024-05-13
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