DFT mechanistic studies of boron–silicon exchange reactions between silyl-substituted arenes and boron bromides

Literature Information

Publication Date 2023-02-13
DOI 10.1039/D2CP05615A
Impact Factor 3.676
Authors

Christopher S. Qiu, Nicholas P. Qiu, Christopher Flinn, Yuming Zhao


View Original

Abstract

C–B bond forming reactions are important methodologies in modern synthetic chemistry, since many borylated organic substrates, ranging from alkanes and alkenes to arenes and heteroarenes, are useful intermediates for the synthesis of natural products, pharmaceuticals, and organic π-conjugated materials. Among numerous borylation methods, C–Si/B–Br exchange reactions have attracted increasing attention in recent years. While experimental exploration has been continually carried out for more than two decades, mechanistic insights into this type of reaction have not yet been clearly established. To address this deficiency of knowledge, we performed density functional theory (DFT) calculations to map out the reaction pathways for a range of boron–silicon exchange reactions between boron tribromide (BBr3) and trimethylsilyl-substituted arenes (TMSAr). Our computational analyses have disclosed the energetic, structural, and electronic properties for key stationary points on the potential energy surfaces (PES) in both the gas and solution (CH2Cl2) phases.

Related Literature

Control of chemical chaos through medium viscosity in a batch ferroin-catalysed Belousov–Zhabotinsky reaction

Marcello A. Budroni, Ilaria Calabrese, Ylenia Miele, Mauro Rustici, Nadia Marchettini, Federico Rossi

2017-11-16 Paper

DOI: 10.1039/C7CP06601E

Influences of polarity and hydration cycles on imbibition hysteresis in silica nanochannels

Carlos Torres-Verdín, Matthew T. Balhoff

2017-11-14 Paper

DOI: 10.1039/C7CP05833K

Back cover

Cover

DOI: 10.1039/C7CP90281F

The benchmark of 31P NMR parameters in phosphate: a case study on structurally constrained and flexible phosphate

Jiří Fukal, Ondřej Páv, Miloš Buděšínský, Jakub Šebera

2017-11-13 Paper

DOI: 10.1039/C7CP06969C

The promoting effect of tetravalent cerium on the oxygen evolution activity of copper oxide catalysts

Zhu Chen, Coleman X. Kronawitter, Xiaofang Yang, Yao-wen Yeh, Nan Yao, Bruce E. Koel

2017-10-18 Paper

DOI: 10.1039/C7CP05248K

Hydrogen sorption efficiency of titanium decorated calix[4]pyrroles

Sandeep Kumar, Rohit Y. Sathe, T. J. Dhilip Kumar

2017-11-20 Paper

DOI: 10.1039/C7CP06781J

Analytical solution of the PELDOR inverse problem using the integral Mellin transform

Alexander G. Maryasov

2017-11-16 Paper

DOI: 10.1039/C7CP04059H

How the hydrogen sorption properties of palladium are modified through interaction with iridium

Christine Goyhenex, Laurent Piccolo

2017-11-22 Paper

DOI: 10.1039/C7CP07155H

Microscopic understanding of the conformational features of a protein–DNA complex

Sandip Mondal, Kaushik Chakraborty

2017-11-21 Paper

DOI: 10.1039/C7CP05161A

You might also like

Compound Q&A

What are the main uses of 1H-Indazole-6-carbonitrile (CAS: 141290-59-7)?

1H-Indazole-6-carbonitrile finds applications in pharmaceuticals, where it serve...

141290-59-71H-Indazole-6-carbon...
Compound Q&A

How should waste containing Dioctyl (2E)-2-butenedioate (CAS: 2997-85-5) be handled?

Waste containing Dioctyl (2E)-2-butenedioate (CAS: 2997-85-5) should be collecte...

2997-85-5Dioctyl (2E)-2-buten...
Compound Q&A

What industries use Sodium [(1,2-benzoxazol-3-ylmethyl)sulfonyl]azanide (CAS: 68291-98-5)?

Sodium [(1,2-benzoxazol-3-ylmethyl)sulfonyl]azanide is primarily used in pharmac...

68291-98-5Sodium [(1,2-benzoxa...
Compound Q&A

Are there alternatives to Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-pyridinedicarboxylate (CAS: 741709-66-0) in synthesis?

Dimethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,6-pyridinedicarboxyla...

741709-66-0Dimethyl 4-(4,4,5,5-...
Compound Q&A

How should waste containing 2-Fluoro-6-hydrazinopyridine (CAS: 80714-39-2) be handled?

Waste containing 2-Fluoro-6-hydrazinopyridine (CAS: 80714-39-2) should be manage...

80714-39-22-Fluoro-6-hydrazino...
Compound Q&A

What is 6-Formyl-2-pyridinecarboxylic acid (CAS: 499214-11-8)?

6-Formyl-2-pyridinecarboxylic acid is an organic compound with the molecular for...

499214-11-86-Formyl-2-pyridinec...
900874-91-13-(3,4-dimethoxyphen...
Compound Q&A

How is 9H-Tribenzo[b,d,f]azepine (CAS: 29875-73-8) typically synthesized?

9H-Tribenzo[b,d,f]azepine is typically synthesized via a multi-step process invo...

29875-73-89H-Tribenzo[b,d,f]az...
Compound Q&A

How is 1-Cyclopropyl-7-ethoxy-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid (CAS: 1797982-51-4) typically synthesized?

1-Cyclopropyl-7-ethoxy-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxyli...

1797982-51-41-Cyclopropyl-7-etho...
Compound Q&A

How should waste containing Methyl 3-oxo-1,2,3,4-tetrahydro-6-quinoxalinecarboxylate (CAS: 671820-52-3) be handled?

Waste containing Methyl 3-oxo-1,2,3,4-tetrahydro-6-quinoxalinecarboxylate (CAS: ...

671820-52-3Methyl 3-oxo-1,2,3,4...

Source Journal

Physical Chemistry Chemical Physics

Physical Chemistry Chemical Physics
CiteScore: 5.5
Self-citation Rate: 10.3%
Articles per Year: 3036

Physical Chemistry Chemical Physics (PCCP) is an international journal co-owned by 19 physical chemistry and physics societies from around the world. This journal publishes original, cutting-edge research in physical chemistry, chemical physics and biophysical chemistry. To be suitable for publication in PCCP, articles must include significant innovation and/or insight into physical chemistry; this is the most important criterion that reviewers and Editors will judge against when evaluating submissions. The journal has a broad scope and welcomes contributions spanning experiment, theory, computation and data science. Topical coverage includes spectroscopy, dynamics, kinetics, statistical mechanics, thermodynamics, electrochemistry, catalysis, surface science, quantum mechanics, quantum computing and machine learning. Interdisciplinary research areas such as polymers and soft matter, materials, nanoscience, energy, surfaces/interfaces, and biophysical chemistry are welcomed if they demonstrate significant innovation and/or insight into physical chemistry. Joined experimental/theoretical studies are particularly appreciated when complementary and based on up-to-date approaches.

Recommended Compounds

Recommended Suppliers

Disclaimer
This page provides academic journal information for reference and research purposes only. We are not affiliated with any journal publishers and do not handle publication submissions. For publication-related inquiries, please contact the respective journal publishers directly.
If you notice any inaccuracies in the information displayed, please contact us at support@chemtradehub.com. We will promptly review and address your concerns.