CAS 1176202-63-3 1,3-Di(1-adamantyl)imidazolinium Tetrafluoroborate

Synonyms

SCHEMBL1078610; CTK4B0351; I14-93977; AKOS015832933; 1,3-Bis(1-adamantyl)imidazolinium tetrafluoroborate; ACMC-2099up; DTXSID30718742; 1176202-63-3;

IUPAC Name

1,3-bis(1-adamantyl)imidazolidin-1-ium;tetrafluoroborate;

Molecular Weight

426.34

Molecular Formula

C23H35BF4N2

Canonical SMILES

[B-](F)(F)(F)F.C1CN(C[NH+]1C23CC4CC(C2)CC(C4)C3)C56CC7CC(C5)CC(C7)C6;

InChI

InChI=1S/C23H36N2.BF4/c1-2-25(23-12-19-6-20(13-23)8-21(7-19)14-23)15-24(1)22-9-16-3-17(10-22)5-18(4-16)11-22;2-1(3,4)5/h16-21H,1-15H2;/q;-1/p+1;

InChI Key

AFLPPSBVXPAHAH-UHFFFAOYSA-O;

Purity

98%

Appearance

Solid

Complexity

517

Covalently-Bonded Unit Count

Exact Mass

428.299g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

428.299g/mol

Rotatable Bond Count

Topological Polar Surface Area

7.7A^2

Application

1,3-Di(1-adamantyl)imidazolinium Tetrafluoroborate is a versatile chiral ligand designed for asymmetric catalysis involving transition metals. It plays a crucial role in facilitating metal-mediated asymmetric reactions such as hydrogenation and disilylation. Notably, this ligand is employed in palladium-catalyzed asymmetric processes, including the arylation of ketones, hydroamination of styrene derivatives, and synthesis of chiral allenes. It also supports rhodium-catalyzed reactions, such as 1,4-additions to enones, hydroboration of cyclopropenes, and C-Si bond formation by conjugate silyl transfer. Additionally, it aids in silver-catalyzed transformations like the Sakuri-Hosomi allylation and Mukaiyama aldol reaction. Its applications extend to various catalytic systems, enhancing enantioselectivity and catalytic activity in processes such as allylation of benzylic alcohols, rearrangement of alkynyl alkenyl carbinols, and asymmetric rearrangement of cyclic enones, underlining its importance as a powerful tool in asymmetric synthesis.

December 25, 2024

Exceptional Catalyst for Asymmetric Reactions

Using Alfa Chemistry's 1,3-Di(1-adamantyl)imidazolinium Tetrafluoroborate in our research greatly enhanced asymmetric catalysis. Its efficiency in selective reactions, like the palladium-catalyzed synthesis of chiral allenes, was remarkable. Highly recommended for consistent results.