Cobalt‐Catalyzed Regioselective Borylation of Arenes: N‐Heterocyclic Silylene as an Electron Donor in the Metal‐Mediated Activation of C−H Bonds
C−H Borylation of arenes has been a subject of great interest recently because of its atom‐economy and the wide applicability of borylated products in value‐added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N‐heterocyclic silylene)‐pyridine pincer ligand (SiNSi) has been synthesiz...
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| Published in | Chemistry : a European journal Vol. 23; no. 24; pp. 5663 - 5667 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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WEINHEIM
Wiley
27.04.2017
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| Abstract | C−H Borylation of arenes has been a subject of great interest recently because of its atom‐economy and the wide applicability of borylated products in value‐added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N‐heterocyclic silylene)‐pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C−H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N‐heterocyclic silylene donors have enormous potential in metal‐catalyzed catalytic applications.
Strong‐armed borylation: A new SiNSi cobalt pincer complex with two N‐heterocyclic silylene (NHSi) arms enabled the direct and facile C−H borylation of heteroarenes and fluorinated arenes with complementary regioselectivity compared to previously reported transition‐metal‐based catalysts. |
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| AbstractList | C-H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in value-added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N-heterocyclic silylene)-pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C-H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N-heterocyclic silylene donors have enormous potential in metal-catalyzed catalytic applications. Strong-armed borylation: A new SiNSi cobalt pincer complex with two N-heterocyclic silylene (NHSi) arms enabled the direct and facile C-H borylation of heteroarenes and fluorinated arenes with complementary regioselectivity compared to previously reported transition-metal-based catalysts. C-H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in value-added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N-heterocyclic silylene)-pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C-H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N-heterocyclic silylene donors have enormous potential in metal-catalyzed catalytic applications.C-H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in value-added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N-heterocyclic silylene)-pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C-H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N-heterocyclic silylene donors have enormous potential in metal-catalyzed catalytic applications. C-H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in value-added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N-heterocyclic silylene)-pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C-H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N-heterocyclic silylene donors have enormous potential in metal-catalyzed catalytic applications. C−H Borylation of arenes has been a subject of great interest recently because of its atom‐economy and the wide applicability of borylated products in value‐added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis( N ‐heterocyclic silylene)‐pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C−H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N‐heterocyclic silylene donors have enormous potential in metal‐catalyzed catalytic applications. C−H Borylation of arenes has been a subject of great interest recently because of its atom‐economy and the wide applicability of borylated products in value‐added synthesis. A new bis(silylene)cobalt(II) complex bearing a bis(N‐heterocyclic silylene)‐pyridine pincer ligand (SiNSi) has been synthesized and structurally characterized. It enabled the regioselective catalytic C−H borylation of pyridines, furans, and fluorinated arenes. Notably, it exhibited complementary regioselectivity for the borylation of fluorinated arenes compared to previously known catalytic systems, demonstrating that N‐heterocyclic silylene donors have enormous potential in metal‐catalyzed catalytic applications. Strong‐armed borylation: A new SiNSi cobalt pincer complex with two N‐heterocyclic silylene (NHSi) arms enabled the direct and facile C−H borylation of heteroarenes and fluorinated arenes with complementary regioselectivity compared to previously reported transition‐metal‐based catalysts. |
| Author | Cui, Chunming Ren, Hailong Driess, Matthias Zhou, Yu‐Peng Bai, Yunping |
| Author_xml | – sequence: 1 givenname: Hailong surname: Ren fullname: Ren, Hailong organization: Nankai University – sequence: 2 givenname: Yu‐Peng surname: Zhou fullname: Zhou, Yu‐Peng organization: Technische Universität Berlin – sequence: 3 givenname: Yunping surname: Bai fullname: Bai, Yunping organization: Nankai University – sequence: 4 givenname: Chunming surname: Cui fullname: Cui, Chunming email: cmcui@nankai.edu.cn organization: Collaborative Innovation Center of Chemical Science and Engineering – sequence: 5 givenname: Matthias surname: Driess fullname: Driess, Matthias organization: Technische Universität Berlin |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28229494$$D View this record in MEDLINE/PubMed |
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| ContentType | Journal Article |
| Copyright | 2017 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | HYDROGENATION C-H borylation COMPLEXES BIS(SILYLENE) cobalt IRON ETHYLENE POLYMERIZATION SILYLATION silylene FUNCTIONALIZATION silicon LIGANDS CONSTRUCTION pincer ligand FLUORINE C−H borylation |
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| Snippet | C−H Borylation of arenes has been a subject of great interest recently because of its atom‐economy and the wide applicability of borylated products in... C-H Borylation of arenes has been a subject of great interest recently because of its atom-economy and the wide applicability of borylated products in... |
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| SubjectTerms | Activation Aromatic compounds Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Cobalt C−H borylation Fluorination Furans Ligands Pesticides Physical Sciences pincer ligand Pyridines Science & Technology silicon silylene Synthesis |
| Title | Cobalt‐Catalyzed Regioselective Borylation of Arenes: N‐Heterocyclic Silylene as an Electron Donor in the Metal‐Mediated Activation of C−H Bonds |
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