Transition-Metal-Free Cross-Coupling of Acetals and Grignard Reagents To Form Diarylmethyl Alkyl Ethers and Triarylmethanes

Yang Qin; Sheng Liu; Shi-Liang Shi

doi:10.1055/a-2088-5000

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(04): 527-538
DOI: 10.1055/a-2088-5000

special topic

Synthetic Development of Key Intermediates and Active Pharmaceutical Ingredients (APIs)

Transition-Metal-Free Cross-Coupling of Acetals and Grignard Reagents To Form Diarylmethyl Alkyl Ethers and Triarylmethanes

Authors

Yang Qin

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610066, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Sheng Liu

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Shi-Liang Shi ∗

^aCollege of Chemistry and Materials Science, Sichuan Normal University, Chengdu 610066, P. R. of China

^bState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China

Abstract

Alle Artikel dieser Rubrik

Abstract

We herein report a transition-metal-free cross-coupling reaction of acetals and Grignard reagents. The method provides a modular preparation of diarylmethyl alkyl ethers, triarylmethanes, and 1,1-diarylalkanes that constitute the core structures of many bioactive molecules and synthetic motifs. A series of readily accessible acetals bearing aryl, alkenyl, and alkyl substituents efficiently coupled with commercially available aryl, alkyl, and allylic magnesium bromides to give the products in high yields. In addition to acyclic and cyclic acetals, ketal and orthoester also serve as viable substrates to afford sterically hindered tertiary ether and ketal respectively. A sequential difunctionalization of acetals led to the rapid synthesis of triarylmethanes and diarylalkanes.

Key words

transition-metal-free - cross-coupling - acetals - Grignard reagents - diarylmethyl alkyl ethers - triarylmethanes

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Referenzen

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