The functionalization of α-C(sp)-H bonds in amines has become a focal point of contemporary research. Here, we report a new approach utilizing photocatalysis α-C(sp)-H bond functionalization in alicyclic and aliphatic secondary amines facilitated by intramolecular 1,5-hydrogen atom transfer (HAT). This finding unlocks a sustainable method for rapidly constructing complex heterocyclics cross-dehydrogenative C-C coupling of protected amines and nitrogen-containing heterocycles. This protocol boasts broad applicability to various substrates, exhibits tolerance to numerous functional groups, and supports the late-stage modification of drug molecules.

Download full-text PDF

Source
http://dx.doi.org/10.1039/d4cc02818jDOI Listing

Publication Analysis

Top Keywords

secondary amines
8
photoredox cross-dehydrogenative
4
cross-dehydrogenative csp-csp
4
csp-csp coupling
4
coupling heteroarenes
4
heteroarenes secondary
4
amines
4
amines 15-hat
4
15-hat functionalization
4
functionalization α-csp-h
4

Similar Publications

In view of the high propensity of tertiary alkyl amines to be bioactive, the development of new methods for their synthesis is an important challenge. Transition-metal catalysis has the potential to greatly expand the scope of nucleophilic substitution reactions of alkyl electrophiles; unfortunately, in the case of alkyl amines as nucleophiles, only one success has been described so far: the selective mono-alkylation of primary amines to form secondary amines. Here, using photoinduced copper catalysis, we report the synthesis of tertiary alkyl amines from secondary amines and unactivated alkyl electrophiles, two readily available coupling partners.

View Article and Find Full Text PDF

The Utility of Preoperative Phenylephrine Testing in Müller Muscle Conjunctival Resection Surgery for Involutional Ptosis.

Ophthalmic Plast Reconstr Surg

January 2025

Division of Orbital and Ophthalmic Plastic Surgery, Jules Stein Eye Institute, University of California, Los Angeles, California, U.S.A.

Purpose: Phenylephrine testing prior to Müller muscle conjunctival resection has traditionally been used to predict postoperative outcomes. The purpose of this study is to determine if preoperative phenylephrine testing impacts postoperative changes in eyelid position.

Methods: In this multicenter cross-sectional cohort study, 270 eyelids of participants with involutional ptosis and levator function >12 mm who underwent Müller muscle conjunctival resection were divided into 2 comparison groups.

View Article and Find Full Text PDF

Introduction: Renal cell carcinoma (RCC) is one of the most common types of urogenital cancer. The introduction of immune-based combinations, including dual immune-checkpoint inhibitors (ICI) or ICI plus tyrosine kinase inhibitors (TKIs), has radically changed the treatment landscape for metastatic RCC, showing varying efficacy across different prognostic groups based on the International Metastatic RCC Database Consortium (IMDC) criteria.

Materials And Methods: This retrospective multicenter study, part of the ARON-1 project, aimed to evaluate the outcomes of favorable-risk metastatic RCC patients treated with immune-based combinations or sunitinib.

View Article and Find Full Text PDF

Acylation represents a pivotal biochemical process that is instrumental in the modification of secondary metabolites throughout the growth and developmental stages of plants. The BAHD acyltransferase family within the plant kingdom predominantly utilizes coenzyme A thioester as the acyl donor, while employing alcohol or amine compounds as the acceptor substrates to facilitate acylation reactions. Using bioinformatics approaches, the gene family members in the genome of () were identified and characterized including gene structure, conserved motifs, -acting elements, and potential gene functions.

View Article and Find Full Text PDF

The objective of this study was to evaluate the efficacy and safety of propranolol hydrochloride tablets and oral solution in neonates with severe IHs. A retrospective cohort study included 184 consecutive neonates diagnosed with severe IHs and treated with propranolol from January 2016 to June 2023. Of these, 126 patients received propranolol tablets, and 58 received propranolol oral solution.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!