Stereodivergent Access to E- and Z-Vinylated Oxindoles via Pd-Catalyzed C(sp3)–H Activation/Heck Coupling, and Energy-Transfer Catalysis

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-20 DOI:10.1021/acs.orglett.6c04320

Saleem Hafeez,Naveen Sihag,Dhanni,M Ramu Yadav

引用次数: 0

Abstract

A one-pot stereodivergent strategy for synthesizing E- and Z-vinylated oxindoles has been developed using a Pd-based tandem catalysis and Pd/Ir relay catalysis. The Pd(0)-catalyzed tandem sequence features a cyclization/C(sp3)–H activation/intermolecular Heck coupling to afford the E-isomer in high yields with excellent stereoselectivities. Integration of this transformation with an Ir-based energy-transfer process in a relay-catalytic mode enables access to the geometrically challenging Z-isomer. The broad substrate scope, late-stage functionalization of bioactive molecules, and synthetic derivatization highlight the method’s utility.

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通过pd催化的C(sp3) - h活化/Heck偶联和能量转移催化获得E-和z -乙烯基氧吲哚

采用Pd基串联催化和Pd/Ir接力催化，建立了一锅立体发散合成E-乙烯基和z -乙烯基氧吲哚的方法。Pd(0)催化的串联序列具有环化/C(sp3) -H活化/分子间Heck偶联的特点，使e -异构体具有高收率和优异的立体选择性。在继电器催化模式下，将这种转化与基于ir的能量转移过程相结合，可以获得几何上具有挑战性的z -异构体。广泛的底物范围，生物活性分子的后期功能化和合成衍生化突出了该方法的实用性。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.