Mechanistic insights into perfluoroaryl borane-catalyzed allylstannations: Toward asymmetric induction with chiral boranes

doi:10.1351/PAC200476030615

Paper

Mechanistic insights into perfluoroaryl borane-catalyzed allylstannations: Toward asymmetric induction with chiral boranes

Published Jan 1, 2004 · D. J. Morrison, J. Blackwell, W. Piers

Pure and Applied Chemistry

Q2 SJR score

15

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

Abstract The perfluoroaryl borane B(C6F5)3 is an effective catalyst for a variety of organic transformations. In the hydrosilation of carbonyl functions, it activates the silane rather than the carbonyl substrate. In allylstannation reactions, two competing reaction pathways are observed, one involving tin cation catalysis, the other "true" borane catalysis. For B(C6F5)3, the former mechanism dominates, while for the weaker Lewis acid PhB(C6F5)2, the latter pathway is more prominent. Thus, chiral boranes of similar Lewis acid strength to PhB(C6F5)2 have the potential to mediate asymmetric allylstannation of aldehyde substrates.

Study Snapshot

Chiral boranes with similar Lewis acid strength to PhB(C6F5)2 could mediate asymmetric allylstannation of aldehyde substrates, potentially enabling asymmetric reactions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Mechanistic insights into perfluoroaryl borane-catalyzed allylstannations: Toward asymmetric induction with chiral boranes

Sign up to use Study Snapshot

References

Citations

The ‘reverse transmetalation’ reaction of the pyrrole-based PNP pincer Ni(II) complexes: X-ray structures of binuclear silver(I) and thiocyanate nickel(II) complexes

The'reverse transmetalation' reaction of pyrrole-based PNP pincer Ni(II) complexes yields a variety of complexes, with structures determined by single crystal X-ray diffraction.

Boron-Based Catalysts for C-C Bond-Formation Reactions.

Boron-based catalysts have shown great success in C-C bond-formation reactions, with four main types: highly Lewis acidic borane, organoboron acids, borenium ions, and other miscellaneous types.

Recent Advances in Boron-Substituted 1,3-Dienes Chemistry: Synthesis and Application.

Boron-substituted 1,3-dienes are useful substrates for various chemical transformations, potentially leading to the syntheses of bioactive natural products with diverse biological activities.

Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic S(N)1 reactions of alcohols.

The strong non-hydrolyzable Lewis acid B(C6F5)3 offers highly chemoselective alcohol substitution in the presence of acid-sensitive alkenes, protecting groups, and other functional groups without compromising reaction rates, substrate scope, and catalyst loading.

Applications of pentafluorophenyl boron reagents in the synthesis of heterocyclic and aromatic compounds.

Pentafluorophenyl boron reagents can be used for the synthesis of heterocyclic and aromatic compounds, with potential applications in catalytic synthesis of aromatic compounds like oxazoles and dibenzopentalene derivatives.

Separating electrophilicity and Lewis acidity: the synthesis, characterization, and electrochemistry of the electron deficient tris(aryl)boranes B(C6F5)(3-n)(C6Cl5)n (n = 1-3).

Electrophilicity increases with substitution of C(6)F(5) for C(6)Cl(5) in electron-deficient tris(aryl)boranes, revealing C(6)Cl(5) to be a more electron-withdrawing group than C(6)F(5).