Catalytic and Base‐free Suzuki‐type α‐Arylation of Cyclic 1,3‐Dicarbonyls via a Cyclic Iodonium Ylide Strategy

Author:

Liang Mingxuan1,He Mengling1,Zhong Zhiqing1,Wan Bei2,Du Qingfeng123,Mai Shaoyu1ORCID

Affiliation:

1. Guangdong Provincial Key Laboratory of Chinese Medicine Pharmaceutics School of Traditional Chinese Medicine Southern Medical University Guangzhou 510515 China

2. Centre of General Practice The Seventh Affiliated Hospital Southern Medical University Foshan 528000 China

3. Integrated Hospital of Traditional Chinese Medicine Southern Medical University Guangzhou 510515 China

Abstract

AbstractTo date, it remains challenging to achieve a general and catalytic α‐arylation of cyclic 1,3‐dicarbonyls, particularly ubiquitous heteroaromatic ones. In most cases, the preparation of their medically significant arylated derivatives requires multistep synthetic sequences. Herein, we introduce a new, convenient strategy involving the conversion of cyclic 1,3‐dicarbonyls to cyclic iodonium ylides (CIYs), followed by rhodium‐catalyzed α‐arylation with arylboronic reagents via carbene coupling. This approach is mild, operationally simple, base‐free, biocompatible, and exhibits broad substrate scope (>100 examples), especially with respect to various heteroaromatic 1,3‐dicarbonyls and ortho‐substituted or base‐sensitive arylboronic acids. Importantly, owing to the excellent compatibility with various arylboronic acids or boronate esters (ArBpin, ArBneop, or ArBF3K), this method allows the late‐stage installation of heterocyclic 1,3‐dicarbonyl motifs in highly complex settings. The utility of this transformation is further demonstrated through significantly simplifying the synthesis of several bioactive molecules and natural products.

Funder

National Natural Science Foundation of China

National Key Research and Development Program of China

Basic and Applied Basic Research Foundation of Guangdong Province

Publisher

Wiley

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