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Organoboron and organosilicon chemistry
Research Guide
What is Organoboron and organosilicon chemistry?
Organoboron and organosilicon chemistry is the study of compounds containing carbon-boron and carbon-silicon bonds, including their synthesis, reactivity, and applications in cross-coupling reactions, frustrated Lewis pairs, and metal-free catalysis.
This field encompasses 37,375 papers on topics such as frustrated Lewis pairs, boronic acids, hydrosilylation, organoboron compounds, and homogeneous catalysis. Key developments include palladium-catalyzed cross-coupling of organoboron derivatives with electrophiles, as reviewed by Suzuki (1999) with 2892 citations. C-H activation methods for C-B bond formation, detailed by Mkhalid et al. (2009) with 2692 citations, enable direct borylation without prefunctionalized substrates.
Topic Hierarchy
Research Sub-Topics
Frustrated Lewis Pairs
Research centers on sterically encumbered Lewis acid-base pairs enabling cooperative reactivity without adduct formation. Studies develop applications in small molecule activation, catalysis, and CO2 reduction.
Organoboron Cross-Coupling Reactions
This field examines Suzuki-Miyaura and related couplings of boronic acids with electrophiles for C-C bond formation. Researchers optimize ligands, conditions, and scope for complex molecule synthesis.
C-H Borylation Reactions
Studies develop catalytic methods for direct C-H to C-B bond conversion using boron reagents. Focus includes regioselectivity, late-stage functionalization, and mechanistic insights.
Hydrosilylation Catalysis
Research investigates transition metal and metal-free catalysts for anti-Markovnikov addition of silanes to unsaturated bonds. Applications span fine chemicals, polymers, and stereoselective processes.
Boronic Acids in Materials Chemistry
This sub-topic covers boronic acid derivatives in optoelectronics, self-healing materials, and sensors via dynamic covalent bonding. Researchers explore photophysical properties and stimuli-responsiveness.
Why It Matters
Organoboron chemistry enables efficient carbon-carbon bond formation through cross-coupling reactions, such as the Suzuki coupling of phenylboronic acid with haloarenes, which Miyaura et al. (1981) demonstrated using palladium catalysis and bases, achieving high selectivity in 1854 cited work. These methods construct complex molecules for pharmaceuticals and materials, with Suzuki (1999) reviewing advances from 1995-1998 that expanded applications to alkenylboranes and alkynyl halides. Frustrated Lewis pairs from organoboron and organosilicon compounds activate hydrogen metal-free, as Welch et al. (2006) showed with a phosphonium borane splitting H2 reversibly (2092 citations), impacting catalysis by reducing reliance on scarce metals. Stephan and Erker (2009) extended this to broader small-molecule activations (1951 citations), supporting sustainable processes in optoelectronics and homogeneous catalysis.
Reading Guide
Where to Start
"Recent advances in the cross-coupling reactions of organoboron derivatives with organic electrophiles, 1995–1998" by Suzuki (1999), as it provides a foundational review of key reactions with 2892 citations, accessible for understanding core synthetic methods.
Key Papers Explained
Suzuki (1999) reviews cross-coupling advances building on earlier work like Miyaura et al. (1979) stereospecific alkenylborane couplings and Miyaura et al. (1981) phenylboronic acid reactions with haloarenes. Mkhalid et al. (2009) extend this by detailing C-H activation for C-B bonds, enabling direct synthesis of boranes used in Suzuki couplings. Welch et al. (2006) introduce metal-free H2 activation via frustrated Lewis pairs, which Stephan and Erker (2009, 2015) develop into broader catalysis platforms incorporating organoboron acids.
Paper Timeline
Most-cited paper highlighted in red. Papers ordered chronologically.
Advanced Directions
Recent perspectives in Stephan and Erker (2015) highlight ongoing small-molecule activations by frustrated Lewis pairs. Main-group systems as transition metals, per Power (2010), suggest frontiers in bond activation without precious metals. The field spans 37,375 papers, focusing on homogeneous catalysis and optoelectronics.
Papers at a Glance
| # | Paper | Year | Venue | Citations | Open Access |
|---|---|---|---|---|---|
| 1 | Recent advances in the cross-coupling reactions of organoboron... | 1999 | Journal of Organometal... | 2.9K | ✕ |
| 2 | C−H Activation for the Construction of C−B Bonds | 2009 | Chemical Reviews | 2.7K | ✕ |
| 3 | A new stereospecific cross-coupling by the palladium-catalyzed... | 1979 | Tetrahedron Letters | 2.2K | ✕ |
| 4 | How to Read and Interpret FTIR Spectroscope of Organic Material | 2019 | Indonesian Journal of ... | 2.1K | ✓ |
| 5 | Reversible, Metal-Free Hydrogen Activation | 2006 | Science | 2.1K | ✕ |
| 6 | Frustrated Lewis Pairs: Metal‐free Hydrogen Activation and More | 2009 | Angewandte Chemie Inte... | 2.0K | ✕ |
| 7 | The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboron... | 1981 | Synthetic Communications | 1.9K | ✓ |
| 8 | Frustrated Lewis Pair Chemistry: Development and Perspectives | 2015 | Angewandte Chemie Inte... | 1.7K | ✕ |
| 9 | Main-group elements as transition metals | 2010 | Nature | 1.6K | ✕ |
| 10 | Cyclometalated Phosphine-Based Pincer Complexes: Mechanistic ... | 2003 | Chemical Reviews | 1.6K | ✕ |
Frequently Asked Questions
What are frustrated Lewis pairs in organoboron chemistry?
Frustrated Lewis pairs are sterically encumbered combinations of Lewis acids like boranes and Lewis bases like phosphines that avoid adduct formation, preserving reactivity. Stephan and Erker (2009) describe their use in metal-free hydrogen activation and more. These pairs enable cooperative substrate binding, as in Welch et al. (2006) where a phosphonium borane reversibly activates H2.
How do cross-coupling reactions use organoboron compounds?
Palladium-catalyzed cross-coupling joins organoboron derivatives like boronic acids with organic electrophiles such as halides. Suzuki (1999) summarizes advances from 1995-1998, including stereospecific couplings of alkenylboranes reported by Miyaura et al. (1979) with 1-alkenyl or 1-alkynyl halides. Miyaura et al. (1981) detail phenylboronic acid coupling with haloarenes in base presence.
What is C-H activation for C-B bond construction?
C-H activation directly functionalizes C-H bonds to form carbon-boron bonds without halide precursors. Mkhalid et al. (2009) review methods using transition metal catalysts for selective borylation. This approach, with 2692 citations, supports synthesis of organoboron compounds for further couplings.
What role do organosilicon compounds play in hydrosilylation?
Hydrosilylation adds Si-H bonds across unsaturated substrates, often catalyzed by frustrated Lewis pairs involving silicon. The field includes organosilicon reactivity within 37,375 papers on homogeneous catalysis. Related developments appear in main-group element activations like those by Power (2010).
What is the current state of frustrated Lewis pair chemistry?
Frustrated Lewis pair chemistry has evolved to activate small molecules beyond hydrogen, including perspectives on development by Stephan and Erker (2015) with 1706 citations. It relies on boron-based Lewis acids paired with sterically hindered bases. Applications span metal-free catalysis and optoelectronics.
Open Research Questions
- ? How can frustrated Lewis pairs be tuned for selective activation of specific unsaturated substrates beyond hydrogen?
- ? What catalysts improve regioselectivity and efficiency in C-H borylation for complex molecule synthesis?
- ? Which steric and electronic factors optimize organoboron compounds for stereospecific cross-couplings with alkynyl electrophiles?
- ? How do main-group organoboron and organosilicon systems mimic transition metal reactivity in bond activation?
- ? What mechanisms govern reversible small-molecule binding in sterically frustrated Lewis pairs?
Recent Trends
The cluster includes 37,375 works on organoboron and organosilicon chemistry, with high-impact reviews like Stephan and Erker on frustrated Lewis pair perspectives (1706 citations) building on their 2009 work (1951 citations).
2015Earlier Suzuki couplings remain foundational, as in the 1999 review (2892 citations).
No preprints or news from the last 12 months available, indicating steady maturation in cross-coupling and metal-free activation.
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