Palladium-Catalyzed Oxidative Borylation of Allylic C-H Bonds in Alkenes.

Org Lett

Institut für Anorganische Chemie and Institute for Sustainable Chemistry & Catalysis with Boron, Julius-Maximilians-Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.

Published: December 2017

This communication describes an efficient palladium pincer complex-catalyzed allylic C-H borylation of alkenes. The transformation exhibits high regio- and stereoselectivity with a variety of linear alkenes. A synthetically useful feature of this allylic C-H borylation method is that all allyl-Bpin products can be isolated in usually high yields. Preliminary mechanistic studies indicate that this C-H borylation reaction proceeds via Pd(IV) pincer complex intermediates.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.7b03296DOI Listing

Publication Analysis

Top Keywords

allylic c-h
12
c-h borylation
12
palladium-catalyzed oxidative
4
borylation
4
oxidative borylation
4
borylation allylic
4
c-h
4
c-h bonds
4
bonds alkenes
4
alkenes communication
4

Similar Publications

Homo-Mannich Reaction of Cyclopropanols: A Versatile Tool for Natural Product Synthesis.

Acc Chem Res

January 2025

Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China.

ConspectusThe Mannich reaction, involving the nucleophilic addition of an enol(ate) intermediate to an imine or iminium ion, is one of the most widely used synthetic methods for the synthesis of β-amino carbonyl compounds. Nevertheless, the homo-Mannich reaction, which utilizes a homoenolate intermediate as the nucleophilic partner and provides straightforward access to the valuable γ-amino carbonyl compounds, remains underexplored. This can be largely attributed to the difficulties in generation and manipulation of the homoenolate species, despite various homoenolate equivalents that have been developed.

View Article and Find Full Text PDF

Palladium-catalyzed allylic C-H alkylation of terminal olefins with 3-carboxamide oxindoles.

Org Biomol Chem

January 2025

Chongqing Research Center for Pharmaceutical Engineering, College of Pharmacy, Chongqing Medical University, Chongqing 400016, China.

A novel palladium-catalyzed allylic C-H alkylation of terminal olefins with 3-carboxamide oxindoles is described. A variety of new 3-carboxamide-3-allylation oxindoles with an all-carbon quaternary center were obtained in moderate to good yields (up to 99%). In addition, the asymmetric version of this reaction was also explored, providing moderate enantioselectivity.

View Article and Find Full Text PDF

A scalable and sustainable electrochemical protocol for allylic C-H aerobic oxidation has been developed, enabling the formation of enones without the use of stoichiometric toxic oxidants or metal catalysts and offering an environmentally benign alternative to traditional chemical oxidation techniques. The process has been successfully applied to selectively oxidize a series of natural products and drug molecules, underscoring its potential for widespread adoption in both academic and industrial contexts.

View Article and Find Full Text PDF

Rhodium(III) catalysis has been used for C-H activation of -nitrosoanilines with substituted allyl alcohols. This method provides an efficient synthesis of the functional -nitroso β-aryl aldehydes and ketones with low catalyst loading, high functional group tolerance, and superior reactivity of allyl alcohols toward -nitrosoanilines. We demonstrated that reaction also proceeds through the one-pot synthesis of -nitrosoaniline, followed by subsequent, C-H activation.

View Article and Find Full Text PDF

Catalytic Asymmetric Oxidative Coupling between C(sp)-H Bonds and Carboxylic Acids.

J Am Chem Soc

January 2025

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.

The direct enantioselective functionalization of C(sp)-H bonds in organic molecules could fundamentally transform the synthesis of chiral molecules. In particular, the enantioselective oxidation of these bonds would dramatically change the production methods of chiral alcohols and esters, which are prevalent in natural products, pharmaceuticals, and fine chemicals. Remarkable advances have been made in the enantioselective construction of carbon-carbon and carbon-nitrogen bonds through the C(sp)-H bond functionalization.

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!