Subtopic Deep Dive

Frustrated Lewis Pair Chemistry
Research Guide

What is Frustrated Lewis Pair Chemistry?

Frustrated Lewis Pair (FLP) chemistry involves sterically hindered Lewis acid-base pairs that cannot form classical adducts, enabling activation of small molecules like H2 and CO2 without transition metals.

FLP systems typically combine electron-deficient boranes with phosphines or amines. Pioneered in main-group catalysis, FLPs achieve metal-free hydrogenation (Scott et al., 2014, 122 citations). Over 500 papers explore FLP variants since 2010.

15
Curated Papers
3
Key Challenges

Why It Matters

FLPs provide sustainable alternatives to scarce transition metals in catalysis, enabling H2 activation for hydrogenation (Scott et al., 2014) and CO2 reduction. Weetman and Inoue (2018, 534 citations) review main-group mimics of metal catalysts, impacting pharmaceutical synthesis. Applications include air-stable borane systems tolerant of diverse solvents (Scott et al., 2014) and isonitrile bond scission (Asakawa et al., 2014, 136 citations), advancing green chemistry processes.

Key Research Challenges

FLP Stability Issues

Many FLPs decompose under reaction conditions due to adduct formation. Scott et al. (2014) address solvent compatibility for air-stable boranes. Thermal robustness remains limited (Herrington et al., 2014).

Substrate Scope Limits

FLPs excel with imines but struggle with unactivated alkenes. Weetman and Inoue (2018) highlight functional group tolerance gaps versus metals. Expanding to CO2 and isonitriles requires new pairs (Asakawa et al., 2014).

Mechanistic Uncertainty

Heterolytic cleavage pathways vary by pair sterics. Inoue et al. (2016, 199 citations) survey N-heterocyclic imines for main-group bonds. NMR studies needed for π-acceptor roles (Vummaleti et al., 2015).

Essential Papers

1.

The Road Travelled: After Main‐Group Elements as Transition Metals

Catherine Weetman, Shigeyoshi Inoue · 2018 · ChemCatChem · 534 citations

Abstract Since the latter quarter of the twentieth century, main group chemistry has undergone significant advances. Power's timely review in 2010 highlighted the inherent differences between the l...

2.

What can NMR spectroscopy of selenoureas and phosphinidenes teach us about the π-accepting abilities of N-heterocyclic carbenes?

Sai V. C. Vummaleti, David J. Nelson, Albert Poater et al. · 2015 · Chemical Science · 277 citations

The relationship between the NMR chemical shifts of phosphinidene and selenourea compounds and the π-accepting ability of the related carbene ligands has been investigated.

3.

Applications of N-heterocyclic imines in main group chemistry

Tatsumi Ochiai, Daniel Franz, Shigeyoshi Inoue · 2016 · Chemical Society Reviews · 199 citations

A survey of the most recent progress in the applications of N-heterocyclic imines in main group compounds is given.

4.

Strategies To Prepare and Use Functionalized Organometallic Reagents

Thomas Klatt, John T. Markiewicz, Christoph Sämann et al. · 2014 · The Journal of Organic Chemistry · 149 citations

Polyfunctional zinc and magnesium organometallic reagents occupy a central position in organic synthesis. Most organic functional groups are tolerated by zinc organometallic reagents, and Csp(2)-ce...

5.

Facile scission of isonitrile carbon–nitrogen triple bond using a diborane(4) reagent

Hiroki Asakawa, Ka‐Ho Lee, Zhenyang Lin et al. · 2014 · Nature Communications · 136 citations

Transition metal reagents and catalysts are generally effective to cleave all three bonds (one σ and two π) in a triple bond despite its high bonding energy. Recently, chemistry of single-bond clea...

6.

Metal‐Free Hydrogenation Catalyzed by an Air‐Stable Borane: Use of Solvent as a Frustrated Lewis Base

Daniel J. Scott, Matthew J. Fuchter, Andrew E. Ashley · 2014 · Angewandte Chemie International Edition · 122 citations

Abstract In recent years ‘frustrated Lewis pairs’ (FLPs) have been shown to be effective metal‐free catalysts for the hydrogenation of many unsaturated substrates. Even so, limited functional‐group...

7.

Dehydrocoupling routes to element–element bonds catalysed by main group compounds

Rebecca L. Melen · 2015 · Chemical Society Reviews · 121 citations

This Tutorial Review focuses on recent applications of main group compounds in the catalytic synthesis of heteronuclear element–element bonds within the p-block.

Reading Guide

Foundational Papers

Start with Scott et al. (2014, 122 citations) for metal-free hydrogenation using solvent bases; Asakawa et al. (2014, 136 citations) for diborane isonitrile scission; Herrington et al. (2014) for silylium-phosphine H2 activation.

Recent Advances

Weetman and Inoue (2018, 534 citations) surveys main-group transition metal mimics; Inoue et al. (2016, 199 citations) covers N-heterocyclic imines; Heilmann et al. (2020, 101 citations) on aluminum imide CO activation.

Core Methods

Steric frustration prevents adducts (Scott 2014); heterolytic H2 splitting; diborane(4) additions (Asakawa 2014); NMR for π-acceptor quantification (Vummaleti 2015).

How PapersFlow Helps You Research Frustrated Lewis Pair Chemistry

Discover & Search

Research Agent uses searchPapers('frustrated Lewis pair hydrogenation') to find Scott et al. (2014, 122 citations), then citationGraph reveals Weetman and Inoue (2018, 534 citations) as highly cited reviewer; exaSearch uncovers niche diborane FLPs from Asakawa et al. (2014).

Analyze & Verify

Analysis Agent applies readPaperContent on Scott et al. (2014) to extract borane-solvent mechanisms, verifyResponse with CoVe cross-checks H2 activation claims against Herrington et al. (2014), and runPythonAnalysis parses NMR shift data from Vummaleti et al. (2015) with GRADE scoring for π-acceptor evidence.

Synthesize & Write

Synthesis Agent detects gaps in FLP substrate scope via contradiction flagging across Weetman (2018) and Inoue (2016); Writing Agent uses latexEditText for reaction schemes, latexSyncCitations for 20+ refs, latexCompile for publication-ready review, and exportMermaid diagrams FLP H2 cleavage pathways.

Use Cases

"Plot citation trends and NMR shifts for FLP boranes from 2010-2020 papers"

Research Agent → searchPapers → Analysis Agent → runPythonAnalysis (pandas/matplotlib on citation/NMR data from Scott 2014, Vummaleti 2015) → researcher gets trend plot and statistical summary.

"Draft LaTeX review on FLP hydrogenation mechanisms citing top 10 papers"

Synthesis Agent → gap detection → Writing Agent → latexEditText + latexSyncCitations (Weetman 2018 et al.) + latexCompile → researcher gets compiled PDF with synced bibliography.

"Find GitHub repos with FLP computational models from recent papers"

Research Agent → paperExtractUrls (Asakawa 2014) → paperFindGithubRepo → githubRepoInspect → researcher gets verified code for diborane(4) simulations.

Automated Workflows

Deep Research workflow scans 50+ FLPs via citationGraph(Weetman 2018), delivering structured report on main-group catalysis evolution. DeepScan's 7-step chain with CoVe verifies mechanisms in Scott et al. (2014) against Inoue (2016). Theorizer generates hypotheses for air-stable FLPs from Herrington (2014) solvent effects.

Frequently Asked Questions

What defines a frustrated Lewis pair?

FLP is a sterically encumbered Lewis acid-base pair preventing classical adduct formation, enabling small molecule activation (Scott et al., 2014).

What are common FLP methods?

Borane-phosphine pairs for H2 cleavage (Herrington et al., 2014); solvent-as-base systems (Scott et al., 2014); diborane(4) for triple bonds (Asakawa et al., 2014).

What are key FLP papers?

Weetman and Inoue (2018, 534 citations) reviews main-group advances; Scott et al. (2014, 122 citations) demonstrates metal-free hydrogenation.

What open problems exist in FLPs?

Thermal stability, broad substrate tolerance, and mechanistic clarity for non-H2 activations (Weetman 2018; Inoue 2016).

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