In 2022,Yang, Peng-Fei; Zhu, Lei; Liang, Jian-Xing; Zhao, Han-Tong; Zhang, Jian-Xin; Zeng, Xian-Wang; Ouyang, Qin; Shu, Wei published an article in ACS Catalysis. The title of the article was 《Regio- and Enantioselective Hydroalkylations of Unactivated Olefins Enabled by Nickel Catalysis: Reaction Development and Mechanistic Insights》.Quality Control of (Bromomethyl)cyclopropane The author mentioned the following in the article:
Direct construction of fully alkyl-substituted tertiary chiral centers remote to activating groups is highly challenging and desirable. Herein, a Ni-catalyzed enantioselective hydroalkylation of unactivated alkenes with unactivated alkyl halides at room temperature is reported, providing a general and practical access to fully alkyl-substituted tertiary stereogenic carbon centers not adjacent to activating groups. This reaction undergoes regio- and stereoselective hydrometalation of unactivated alkenes with a nontrivial Markovnikov selectivity, followed by cross-coupling with unactivated alkyl electrophiles to access trialkyl tertiary saturated stereogenic centers not adjacent to activating groups. The mild and robust conditions enable the use of terminal and internal unactivated alkenes and unactivated primary and secondary alkyl, benzyl and propargyl halides to construct diverse trialkyl tertiary stereogenic carbon centers with broad functional group tolerance. Moreover, exptl. investigations support the reaction undergoing irreversible and stereoselective hydrometalation of alkenes. D. functional theory calculations provide further insights into the reaction mechanism, suggesting a stereoselective migration insertion of alkenes with Ni(II)-H species. Finally, the origin of the regio- and enantioselectivities was also investigated. In the experiment, the researchers used (Bromomethyl)cyclopropane(cas: 7051-34-5Quality Control of (Bromomethyl)cyclopropane)
(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.Quality Control of (Bromomethyl)cyclopropane
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary