- Rhodium-Catalyzed ortho-Selective C-F Bond Borylation of Polyfluoroarenes with Bpin-Bpin
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An ortho-selective C-F bond borylation between N-heterocycle-substituted polyfluoroarenes and Bpin-Bpin with simple and commercially available [Rh(cod)2]BF4 as a catalyst is now reported. The reaction proceeds under mild reaction con
- Guo, Wen-Hao,Min, Qiao-Qiao,Gu, Ji-Wei,Zhang, Xingang
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- Ru-Catalyzed ortho-Selective Diborylation of 2-Arylpyridines toward the Construction of ?-Conjugated Functions
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A ruthenium catalytic ortho-C-H diborylation of 2-arylpyridine derivatives, including challenging 2-phenoxypyridine functions, using a remarkably low catalyst loading and a low-cost and bench-stable boron source, has been developed. The novel strategy shows high activity with excellent selectivity and may offer a versatile and green alternative to currently employed high loadings of noble metals or extra additives for the selective borylations.
- Yao, Wubing,Wang, Jiali,He, Lili,Cao, Dongdong,Yang, Jianguo
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- Ruthenium(II) Biscarboxylate-Catalyzed Borylations of C(sp2)?H and C(sp3)?H Bonds
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Versatile borylations of C(sp2)?H and C(sp3)?H were achieved with ruthenium(II) biscarboxylate complexes. The robust nature of the ruthenium(II) catalyst enabled C(sp3)?H borylation on pyrrolidines, piperidines, and azepan
- Sarkar, Suman De,Kumar, N. Y. Phani,Ackermann, Lutz
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- Photo-Induced ortho-C-H Borylation of Arenes through in Situ Generation of Rhodium(II) Ate Complexes
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Photoinduced in situ "oxidation"of half-sandwich metal complexes to "high-valent"cationic metal complexes has been used to accelerate catalytic reactions. Here, we report the unprecedented photoinduced in situ "reduction"of half-sandwich metal [Rh(III)] complexes to "low-valent"anionic metal [Rh(II)] ate complexes, which facilitate ligand exchange with electron-deficient elements (diboron). This strategy was realized by using a functionalized cyclopentadienyl (CpA3) Rh(III) catalyst we developed, which enabled the basic group-directed room temperature ortho-C-H borylation of arenes.
- Araujo Dias, Ant?nio Junio,Nagashima, Yuki,Tanaka, Jin,Tanaka, Ken
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supporting information
p. 11325 - 11331
(2021/08/03)
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- N-heterocyclic carbene enabled rhodium-catalyzed ortho C(sp2)-H borylation at room temperature
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We report a rhodium-catalyzed ortho C(sp2)-H borylation of 2-phenylpyridines using commercially available N-heterocyclic carbenes (NHCs) as ligand and pinacolatodiboron (B2pin2) as borylating reagent. The reaction could take place at room temperature, tolerating a wide range of functionalities and affording ortho borylated products in moderate to excellent yields. The current method is also applicable to gram-scale reaction with reduced catalyst loading.
- Zhong, Lei,Zong, Zhi-Hong,Wang, Xi-Cun
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p. 2547 - 2552
(2019/03/27)
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- Visible Light Induced Rhodium(I)-Catalyzed C?H Borylation
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An efficient visible light induced rhodium(I)-catalyzed regioselective borylation of aromatic C?H bonds is reported. The photocatalytic system is based on a single NHC?RhI complex capable of both harvesting visible light and enabling the bond breaking/forming at room temperature. The chelating nature of the NHC-carboxylate ligand was critical to ensure the stability of the RhI complex and to provide excellent photocatalytic activities. Experimental mechanistic studies evidenced a photooxidative ortho C?H bond addition upon irradiation with blue LEDs, leading to a cyclometalated RhIII-hydride intermediate.
- Thongpaen, Jompol,Manguin, Romane,Dorcet, Vincent,Vives, Thomas,Duhayon, Carine,Mauduit, Marc,Baslé, Olivier
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supporting information
p. 15244 - 15248
(2019/10/22)
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- Directed: Ortho C-H borylation catalyzed using Cp?Rh(iii)-NHC complexes
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Cp?Rh(NHC) complexes with bulky chiral bidentate NHC-carboxylate ligands were efficiently synthesized and fully characterized including solid-state structures. These unprecedented rhodium(iii) complexes demonstrated high selectivity in pyridine-directed ortho-C-H borylation of arenes under mild conditions.
- Thongpaen, Jompol,Schmid, Thibault E.,Toupet, Loic,Dorcet, Vincent,Mauduit, Marc,Baslé, Olivier
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supporting information
p. 8202 - 8205
(2018/07/29)
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- Ruthenium catalysed C-H bond borylation
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An easily prepared series of phenylindenyldihydridosilyl ruthenium complexes (2a-2d) was obtained by reaction of tertiary silanes with the commercially-available [RuCl(3-phenylindenyl)(PPh3)2] (1). The [RuH2(3-phenylindeny
- Fernández-Salas, José A.,Manzini, Simone,Piola, Lorenzo,Slawin, Alexandra M. Z.,Nolan, Steven P.
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supporting information
p. 6782 - 6784
(2014/06/23)
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- Silyl phosphorus and nitrogen donor chelates for homogeneous ortho borylation catalysis
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Ir catalysts supported by bidentate silyl ligands that contain P- or N-donors are shown to effect ortho borylations for a range of substituted aromatics. The substrate scope is broad, and the modular ligand synthesis allows for flexible catalyst design.
- Ghaffari, Behnaz,Preshlock, Sean M.,Plattner, Donald L.,Staples, Richard J.,Maligres, Peter E.,Krska, Shane W.,Maleczka, Robert E.,Smith, Milton R.
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supporting information
p. 14345 - 14348
(2014/12/10)
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- Rh-catalyzed ortho -selective C-H borylation of N-functionalized arenes with silica-supported bridgehead monophosphine ligands
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Supported phosphine-Rh systems, prepared in situ from silica-supported bridgehead monophosphines and [Rh(OH)(cod)]2, have enabled ortho-selective C-H borylation for a range of arenes containing nitrogen-based directing groups. The regioselectivity was excellent with various N-directing groups, including saturated and unsaturated N-heterocycles, tert-aminoalkyl groups, and imine-type C-N double bonds. The reaction showed significant tolerance toward steric repulsion around the reacting C-H bond. This Rh catalysis complements the Ir-catalyzed ortho-borylation, which is effective for arenes with oxygen-based directing groups.
- Kawamorita, Soichiro,Miyazaki, Tatsuya,Ohmiya, Hirohisa,Iwai, Tomohiro,Sawamura, Masaya
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p. 19310 - 19313
(2012/01/15)
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