In 2022,Rodrigalvarez, Jesus; Reeve, Luke A.; Miro, Javier; Gaunt, Matthew J. published an article in Journal of the American Chemical Society. The title of the article was 《Pd(II)-Catalyzed Enantioselective C(sp3)-H Arylation of Cyclopropanes and Cyclobutanes Guided by Tertiary Alkylamines》.Formula: C4H7Br The author mentioned the following in the article:
Here, a palladium-catalyzed enantioselective C(sp3)-H arylation of aminomethyl-cyclopropanes I [R = H, Me, (CH2)2OMe, 4-ClC6H44; R1 = NMe2, NEt2, N-piperidinyl, etc.; Ar = Ph, 2-naphthyl, 6-Cl-3-pyridinyl, etc.; n = 1] and -cyclobutanes I [n = 2] with aryl boronic acids was reported. A range of native tertiary alkylamine groups were able to direct C-H cleavage and forge carbon-aryl bonds on the strained cycloalkanes framework as single diastereomers and with excellent enantiomeric ratios. Central to the success of this strategy was the use of a simple N-acetyl amino acid ligand, which not only controls the enantioselectivity but also promotes γ-C-H activation of over other pathways. Computational anal. of the cyclopalladation step provided an understanding of how enantioselective C-H cleavage occurred and revealed distinct transition structures to our previous work on enantioselective desymmetrization of N-iso-Bu tertiary alkylamines. This straightforward and operationally simple method simplified the construction of functionalized aminomethyl-strained cycloalkanes, which was believed will find widespread use in academic and industrial settings relating to the synthesis of biol. active small mols.(Bromomethyl)cyclopropane(cas: 7051-34-5Formula: C4H7Br) was used in this study.
(Bromomethyl)cyclopropane(cas: 7051-34-5) is used as a synthetic building block for the introduction of the cyclopropylmethyl group. It was also used in the synthesis of 1,4-dienes via iron-catalyzed cross-coupling with alkenyl Grignard reagents.Formula: C4H7Br
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary