Photocatalytic α‐Tertiary Amine Synthesis via C−H Alkylation of Unmasked Primary Amines

Abtract

A) Prior art for catalytic α‐C−H alkylation of primary amines; B) This work. EWG=electron‐withdrawing group.

A practical, catalytic entry to α,α,α‐trisubstituted (α‐tertiary) primary amines by C−H functionalisation has long been recognised as a critical gap in the synthetic toolbox. We report a simple and scalable solution to this problem that does not require any in situ protection of the amino group and proceeds with 100 % atom‐economy. Our strategy, which uses an organic photocatalyst in combination with azide ion as a hydrogen atom transfer (HAT) catalyst, provides a direct synthesis of α‐tertiary amines, or their corresponding γ‐lactams. We anticipate that this methodology will inspire new retrosynthetic disconnections for substituted amine derivatives in organic synthesis, and particularly for challenging α‐tertiary primary amines.

Authors: Alison S. H. Ryder Dr. William B. Cunningham George Ballantyne Tom Mules Anna G. Kinsella Jacob Turner‐Dore Dr. Catherine M. Alder Lee J. Edwards Dr. Blandine S. J. McKay Dr. Matthew N. Grayson Dr. Alexander J. Cresswell

Link
https://onlinelibrary.wiley.com/doi/full/10.1002/anie.202005294#.Xr2aciKIkvU.twitter

 

Lucent 360, photoredox, C-N couplings

Lucent360 Customized Reaction Screenings

Learn how to streamline with Lucent360 customized reaction screenings and save on time & setups when matching optimal wavelength to a photocatalyst.

Upcycling Plastic Using Light

Photocatalytic Deconstruction of Polystyrene

What if we could shine a blue LED on our 8 billion tons of plastic waste and get back a valuable chemical feedstock? Click to read about the Reisner group’s work looking at tackling this problem.

photocatalysis in seawater

Photocatalysis in Seawater

Seawater: It’s abundant, messy, contains salts, microorganisms, biomass, organic and inorganic pollutants (and microplastics) and might just be a great solvent for generating hydrogen peroxide with visible light photocatalysis

Comparing Commercial Photoreactors

How should we compare commercial photoreactors? Or better yet, how do we discuss the important details of a photochemical reaction?

The 21 Must-Read Photochemistry Papers of 2021

Beyond the best photochemistry papers of 2021, read about the amazing year we had here at HepatoChem.

Utilizing the Lucent360 From Screen to Scale

Read on for a step by step study taking a photocatalyzed-Arbuzov reaction from screen to scale utilizing the unique features of the Lucent360™

Introducing the Lucent360

The Lucent360’s flexible design gives you the best options to learn everything you need to know to take your photochemical reactions from screen to scale.

Photochemistry of earth-abundant metals

A recurring theme in our recent articles: there isn’t enough iridium or ruthenium in the earth’s crust to do all the photochemistry we’d like to do at scale.

Contact Us

Interested in learning more about our products?

Complete our short contact form and we’ll get back to you as soon as possible.

Stay up-to-date!
Get insights and tips from experts