Nickel-Catalysed Allylboration of Aldehydes

Saturated heterocycles are found widely in biologically active compounds such as medicinal drugs and agrochemicals. However, boronic acid‐derived building blocks for these structures have limited availability, particularly in comparison to heteroaromatic boronic acids. We report the preparation of boronic ester γ‐lactams through a Cu‐catalysed conjugate borylation‐cyclisation protocol. Using a chiral catalyst, this can be performed in high enantioselectivity. Exploration of the further transformations of these reagents suggest that the boronic esters have much potential as chemical building blocks.

show abstract

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Rodgers

Wilson

Robertson

et al. 2020

Adv Synth Catal

Self Cite

View full text Add to dashboard Cite

show abstract

Chan–Lam Amination of Secondary and Tertiary Benzylic Boronic Esters

et al. 2021

Self Cite

View full text Add to dashboard Cite

We report a Chan–Lam coupling reaction of benzylic and allylic boronic esters with primary and secondary anilines to form valuable alkyl amine products. Both secondary and tertiary boronic esters can be used as coupling partners, with mono-alkylation of the aniline occurring selectively. This is a rare example of a transition-metal-mediated transformation of a tertiary alkylboron reagent. Initial investigation into the reaction mechanism suggests that transmetalation from B to Cu occurs through a single-electron, rather than a two-electron process.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Nickel-Catalysed Allylboration of Aldehydes

Cited by 2 publications

References 22 publications

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Synthesis of Boronic Ester γ‐Lactam Building Blocks

Chan–Lam Amination of Secondary and Tertiary Benzylic Boronic Esters

Contact Info

Product

Resources

About