Allylation of C‐, N‐, and O‐Nucleophiles via a Mechanochemically‐Driven Tsuji–Trost Reaction Suitable for Late‐Stage Modification of Bioactive Molecules DOI Creative Commons
Johanna Templ, Michael Schnürch

Angewandte Chemie, Год журнала: 2023, Номер 136(1)

Опубликована: Ноя. 6, 2023

We present the first solvent-free, mechanochemical protocol for a palladium-catalyzed Tsuji-Trost allylation. This approach features exceptionally low catalyst loadings (0.5 mol %), short reaction times (<90 min), and simple setup, eliminating need air or moisture precautions, making process highly efficient environmentally benign. introduce solid, nontoxic, easy-to-handle allyl trimethylammonium salts as valuable alternative to volatile hazardous reagents. Our enables allylation of various

Язык: Английский

A Guide for Mono‐Selective N‐Methylation, N‐Ethylation, and N‐n‐Propylation of Primary Amines, Amides, and Sulfonamides and Their Applicability in Late‐Stage Modification DOI Creative Commons
Johanna Templ, Michael Schnürch

Chemistry - A European Journal, Год журнала: 2024, Номер 30(26)

Опубликована: Фев. 14, 2024

Abstract This review provides a comprehensive overview of mono‐alkylation methodologies targeting crucial nitrogen moieties – amines, amides, and sulfonamides found in organic building blocks pharmaceuticals. Emphasizing the intersection chemical precision with drug discovery, central challenge addressed is achieving one‐pot mono‐selective short‐chain N‐alkylations (methylations, ethylations, n ‐propylations), preventing undesired overalkylation. Additionally, sustainable, safe, benign alternatives to traditional alkylating agents, including alcohols, carbon dioxide, carboxylic acids, nitriles, alkyl phosphates, quaternary ammonium salts, carbonates, are explored. review, categorized by nature agent, aids researchers selecting suitable methods for N‐alkylation.

Язык: Английский

Процитировано

7

Allylation of C‐, N‐, and O‐Nucleophiles via a Mechanochemically‐Driven Tsuji–Trost Reaction Suitable for Late‐Stage Modification of Bioactive Molecules DOI Creative Commons
Johanna Templ, Michael Schnürch

Angewandte Chemie International Edition, Год журнала: 2023, Номер 63(1)

Опубликована: Ноя. 6, 2023

Abstract We present the first solvent‐free, mechanochemical protocol for a palladium‐catalyzed Tsuji–Trost allylation. This approach features exceptionally low catalyst loadings (0.5 mol %), short reaction times (<90 min), and simple setup, eliminating need air or moisture precautions, making process highly efficient environmentally benign. introduce solid, nontoxic, easy‐to‐handle allyl trimethylammonium salts as valuable alternative to volatile hazardous reagents. Our enables allylation of various O ‐, N C ‐nucleophiles in yields up 99 % even structurally complex bioactive compounds, owing its mild conditions exceptional functional group tolerance.

Язык: Английский

Процитировано

12

Mechanochemical aerobic oxidative Heck coupling by polymer-assisted grinding: cyclodextrin additive facilitating regioselectivity control DOI
Keyu Xiang, Haowen Shou, Chenhui Hu

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(10), С. 5890 - 5899

Опубликована: Янв. 1, 2024

A novel approach utilizing the polymer-assisted grinding (POLAG) technique to facilitate regioselective oxidative Heck coupling of aryl boronic acids with electronically unbiased olefins under solvent-free conditions was presented.

Язык: Английский

Процитировано

4

Tech Business Analytics in Quaternary Industry Sector DOI Open Access
Sachin Kumar, Krishna Prasad K, P. S. Aithal

и другие.

International Journal of Case Studies in Business IT and Education, Год журнала: 2024, Номер unknown, С. 69 - 159

Опубликована: Апрель 19, 2024

Purpose: The knowledge-based segment of the economy is referred to as "quaternary sector," which comprises businesses like information technology, telecommunications, research and development, other professional services. Businesses in this industry may find that technology-driven business analytics greatly aids helping them make data-driven decisions, optimize workflows, enhance overall performance. Utilizing technology analyse can significantly improve market trends, consumer behaviour, an organization's operational Through analysis data, companies more informed decisions support expansion competitiveness. Analytics tools assist identifying inefficiencies their processes operations so they changes reduce expenses, boost output, ultimately revenue. Customer loyalty satisfaction rise a result this. Information regarding emerging technologies integration with data science prediction trends could present chances for growth innovation. Methodology: There are particular potential challenges Quaternary sector because its emphasis on activities, innovation, cutting-edge technology. Here, we methodical strategy using industry, allowing obtain useful long-term planning calculations. This approach gives framework utilizing analytics. helps competitive advantages increasingly environment by access important insights spur Findings/Result: study looks at how digital have been used control from birth present. Originality/Value: An explanation tech differs traditional within industry. It also includes general design be technical purposes, it examines thirty recently submitted recommendations related Tech Business industries. Paper Type: Exploratory research.

Язык: Английский

Процитировано

4

Strategies for Using Quaternary Ammonium Salts as Alternative Reagents in Alkylations DOI Creative Commons
Johanna Templ, Michael Schnürch

Chemistry - A European Journal, Год журнала: 2024, Номер 30(33)

Опубликована: Апрель 8, 2024

Alkylation reactions are pivotal in organic chemistry, with wide-ranging utilization across various fields of applied synthetic chemistry. However, conventional reagents employed alkylations often pose substantial health and exposure risks. Quaternary ammonium salts (QAS) present a promising alternative for these transformations offering significantly reduced hazards as they non-cancerogenic, non-mutagenic, non-flammable, non-corrosive. Despite their potential, use direct remains relatively unexplored. This review outlines strategies utilizing QAS alkylation reactions, providing researchers safer approaches to chemical synthesis.

Язык: Английский

Процитировано

3

Palladium-catalyzed allylic C-H alkylation of terminal olefins with 3-carboxamide oxindoles DOI
Ning Zhang,

Guojuan Liang,

Dexin Zhang

и другие.

Organic & Biomolecular Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Янв. 1, 2025

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

Язык: Английский

Процитировано

0

Advances in Mechanochemical C─H Functionalization: A Comparative Study with Solvent‐Based Approaches DOI Creative Commons
N. Narayanan, Michael Schnürch

ChemCatChem, Год журнала: 2025, Номер unknown

Опубликована: Май 31, 2025

Abstract This review provides an overview on recent progress in mechanochemical transition metal catalyzed C─H functionalization. Solventless operation and enhanced reaction efficiency makes synthesis a more sustainable alternative to conventional approaches. By including comparison between methods solvent‐based protocols, this chemists with valuable insights into the relative sustainability of these solventless strategies. enables informed decision‐making when selecting for functionalization based specific needs. Moreover, identifies existing gaps discusses necessary steps establish it as mainstream approach. bridging gaps, can further enhance utility adoption methodologies, contributing practices synthetic chemistry.

Язык: Английский

Процитировано

0

High‐Energy Ball Milling Enables an Ultra‐fast Wittig Olefination Under Ambient and Solvent‐free Conditions DOI Creative Commons
Johanna Templ, Michael Schnürch

Angewandte Chemie International Edition, Год журнала: 2024, Номер 63(49)

Опубликована: Авг. 29, 2024

Abstract 30 Seconds to success!—The Wittig reaction, a fundamental and extensively utilized reaction in organic chemistry, enables the efficient conversion of carbonyl compounds olefins using phosphonium salts. Traditionally, meticulous setup, including pre‐formation reactive ylide species via deprotonation salt, is crucial for achieving high‐yielding reactions under classical solution‐based conditions. In this report, we present an unprecedented protocol ultra‐fast mechanically induced solvent‐free ambient conditions, often eliminating need tedious strict air moisture exclusion. A range aldehydes ketones were reacted with diverse salts high‐energy ball milling frequently giving access respective only seconds.

Язык: Английский

Процитировано

2

High-speed Ball Milling Enables an Ultra-fast Wittig Olefination Under Ambient and Solvent-free Conditions Without Ylide Pre-formation DOI Creative Commons
Johanna Templ, Michael Schnürch

Опубликована: Июнь 17, 2024

30 Seconds to success! – The Wittig reaction, a fundamental and extensively utilized reaction in organic chemistry, enables the efficient conversion of carbonyl compounds olefins using phosphonium salts. Traditionally, meticulous setup, including pre-formation reactive ylide species via deprotonation salt, is crucial for achieving high-yielding reactions under classical solution-based conditions. In this report, we present an unprecedented protocol ultra-fast mechanochemically driven solvent-free ambient conditions, eliminating need tedious strict air moisture exclusion. A range aldehydes ketones were reacted with diverse salts high-speed ball milling giving access respective only seconds.

Язык: Английский

Процитировано

1

Mechanochemical Ball Milling Approach to C(sp3)‐H Functionalization of 8‐Methylquinolines DOI Creative Commons
N. Narayanan, Michael Schnürch

ChemCatChem, Год журнала: 2024, Номер unknown

Опубликована: Дек. 23, 2024

Abstract A mechanochemical, highly regioselective rhodium(III)‐catalyzed C─H methylation of 8‐methylquinolines is reported. The method reported in this study, often solvent‐free or uses minimal solvent (liquid assisted grinding), operates without external heating under mild reaction conditions, demonstrating tolerance for various functional groups. Moreover, the time significantly reduced compared to solvent‐based variant. Notably, can be carried out using a pestle and mortar instead ball milling as well, highlighting operational simplicity approach achieving challenging C(sp 3 )‐H activation more sustainable conditions.

Язык: Английский

Процитировано

1