Affiliation:
1. College of Chemistry and Materials Science, Sichuan Normal University
2. State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences
Abstract
AbstractWe 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.
Funder
National Key Research and Development Program of China
National Natural Science Foundation of China
Program of Shanghai Academic Research Leader
Subject
Organic Chemistry,Catalysis
Cited by
1 articles.
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