1632070-95-1Relevant academic research and scientific papers
Palladium-Catalyzed Hiyama Coupling of Benzylic Ammonium Salts via C-N Bond Cleavage
Han, Chunyu,Zhang, Zhenming,Xu, Silin,Wang, Kai,Chen, Kaiting,Zhao, Junfeng
, p. 16308 - 16313 (2019)
The first palladium-catalyzed Hiyama cross-coupling of arylsilanes with benzyltrimethylammonium salts is reported. The reaction proceeds smoothly to facilitate C(sp2)-C(sp3) bond formation via cleavage of the C-N bond and provides a useful approach to various diarylmethanes with a broad substrate scope and excellent functional group tolerance in good to excellent yields.
Palladium catalyzed Suzuki cross-coupling of benzyltrimethylammonium salts via C-N bond cleavage
Wang, Tao,Yang, Shuwu,Xu, Silin,Han, Chunyu,Guo, Ge,Zhao, Junfeng
, p. 15805 - 15808 (2017/03/22)
A palladium catalyzed Suzuki cross-coupling for construction of Csp3-Csp2 bond via Csp3-N bond activation of benzyltrimethyl-ammonium salt is described. This reaction not only offered a highly efficient approach to diarylmethanes but also paved the way for the application of benzyltrimethylammonium salts in the palladium catalyzed cross coupling reactions.
Single-electron transmetalation in organoboron cross-coupling by photoredox/nickel dual catalysis
Tellis, John C.,Primer, David N.,Molander, Gary A.
, p. 433 - 436 (2014/08/05)
The routine application of Csp3-hybridized nucleophiles in cross-coupling reactions remains an unsolved challenge in organic chemistry. The sluggish transmetalation rates observed for the preferred organoboron reagents in such transformations are a consequence of the two-electron mechanism underlying the standard catalytic approach. We describe a mechanistically distinct single-electron transfer-based strategy for the activation of organoboron reagents toward transmetalation that exhibits complementary reactivity patterns. Application of an iridium photoredox catalyst in tandem with a nickel catalyst effects the cross-coupling of potassium alkoxyalkyl- and benzyltrifluoroborates with an array of aryl bromides under exceptionally mild conditions (visible light, ambient temperature, no strong base). The transformation has been extended to the asymmetric and stereoconvergent cross-coupling of a secondary benzyltrifluoroborate.
