Rh(I)‐Catalyzed Decarboxylative Arylation of Alkynyl Cyclic Carbonates: Divergent Access to Substituted α‐Allenols and 1,3‐Butadienes

IF 4.4 2区 化学 Q2 CHEMISTRY, APPLIED
Geetanjali S. Sontakke , Rahul K. Shukla , Chandra M.R. Volla
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引用次数: 0

Abstract

Rh(I)‐catalyzed decarboxylative arylation of alkynyl cyclic carbonates using commercially available and low‐toxic aryl boronic acids has been disclosed. Depending on the nature of the cyclic carbonates, the methodology provides a straightforward platform to access either substituted 2,3‐allenols or 1,3‐butadiene derivatives. Internal alkynyl cyclic carbonates undergo monoarylation to conveniently afford 2,3‐allenols with high syn‐selectivity for the aryl and hydroxy groups. Whereas, terminal alkynyl carbonates led to the formation of diarylated 1,3‐butadiene derivatives having cis‐configuration for the two aryl groups via allenyl rhodium(I)alkoxide intermediate. The compatibility of various functional groups allowed to develop a library of diversely functionalized scaffolds with excellent regioselectivity in good yields. Late‐stage transformation of a series of natural products highlights the wide applicability of the arylation process. Additionally, scale‐up experiments and downstream transformations of α‐allenol derivatives into other valuable heterocycles illustrate the efficacy of the protocol.

Rh(I)‐催化的烷基环碳酸盐脱羧芳基化:取代α‐烯醇和1,3‐丁二烯的不同途径
利用市售的低毒芳基硼酸,Rh(I)催化羰基环碳酸酯脱羧。根据环状碳酸盐的性质,该方法提供了一个直接的平台来获取取代的2,3 -烯醇或1,3 -丁二烯衍生物。内部炔基环碳酸盐经过单芳基化,方便地产生2,3 -烯烯醇,对芳基和羟基具有高syn选择性。而末端的炔基碳酸酯则通过烯基铑(I)醇氧化合物中间体生成具有两个芳基的顺式构型的二芳化1,3 -丁二烯衍生物。各种官能团的相容性允许开发具有优异区域选择性和高收率的多种功能化支架库。一系列天然产物的后期转化突出了芳基化过程的广泛适用性。此外,大规模实验和α -烯醇衍生物下游转化为其他有价值的杂环也证明了该方案的有效性。
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来源期刊
Advanced Synthesis & Catalysis
Advanced Synthesis & Catalysis 化学-应用化学
CiteScore
9.40
自引率
7.40%
发文量
447
审稿时长
1.8 months
期刊介绍: Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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