Highly Regioselective Synthesis of Indene Derivatives Including an Allene Functional Group via Pd/C-Catalyzed Cyclization Reaction in Air

Bi, Hai‐Peng; Liu, Xueyuan; Gou, Fa‐Rong; Guo, Li‐Na; Duan, Xin‐Hua; Liang, Yong‐Min

doi:10.1021/ol071385u

Cited by 56 publications

(18 citation statements)

References 24 publications

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“…28 The reaction was found to be highly regioselective in favor of the formation of a 5-membered ring in 78, appended with an exocyclic allene, rather than a 6-membered ring arising from addition to the central carbon atom of a  ate. As such, an enolate of the malonate underwent a cyclization to install a quaternary center, and a range of allenes 78a-d were obtained in the absence of an external nucleophile.…”

Section: Scheme 14 Cyclization With Tethered Carbon Nucleophiles In mentioning

confidence: 97%

Palladium-catalyzed construction of quaternary carbon centers with propargylic electrophiles

Franckevičius

2016

Tetrahedron Letters

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This short review describes the broad reactivity of propargylic electrophiles with nucleophiles under palladium catalysis for the construction of quaternary carbon centers, leading to allenylation, propargylation and alkenylation / allylic alkylation. Although the allenylation and propargylation of a nucleophile can readily create congested carbon centers, these processes often compete and require careful tuning of substrate structure and reactivity of the nucleophile. The alkenylation / allylic alkylation sequence is a much more studied reactivity mode, which results in the coupling of two nucleophiles. This approach is very popular for the rapid generation of molecular complexity, but also poses several chemo-and regioselectivity issues. These selectivity problems have been traditionally overcome by tethering strategies and cyclization reactions. However, over the past few years, highly selective intermolecular coupling reactions of nucleophiles have also been developed. It is, therefore, unsurprising that, as our prowess to control selectivity has grown, the first methods for the palladium-catalyzed enantioselective installation of quaternary carbon centers with propargylic electrophiles have also appeared.

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Section: Scheme 14 Cyclization With Tethered Carbon Nucleophiles In mentioning

confidence: 97%

Palladium-catalyzed construction of quaternary carbon centers with propargylic electrophiles

Franckevičius

2016

Tetrahedron Letters

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“…Alkyl propargyl carbonates and analogues are known to react with Pd 0 with formation of an allenylpalladium(II) complex with elimination of the alkylcarbonate as the leaving group. This reactivity was exploited for the synthesis of allenylindane derivatives, starting from propargylic substrates bearing a carbonucleophile in a suitable position, as exemplified in Scheme for the formation of diethyl 1‐alkylidenindane‐2,2‐dicarboxylates 117 starting from diethyl 2‐(2‐(3‐(ethoxycarbonyloxy)prop‐1‐ynyl)benzyl)malonates and analogues 116 . The possibility to carry out the reaction under phase‐transfer catalysis (PTC) in the absence of metals has also been reported …”

Section: Synthesis Of Indanesmentioning

confidence: 99%

“… Synthesis of 1‐allenylindane derivatives 117 by Pd 0 ‐catalyzed carbocyclization of diethyl 2‐(2‐(3‐(ethoxycarbonyloxy)prop‐1‐ynyl)benzyl)malonates and analogues 116 …”

Section: Synthesis Of Indanesmentioning

confidence: 99%

Recent Advances in the Synthesis of Indanes and Indenes

Gabriele

Mancuso

Veltri

2016

Chemistry A European J

172

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Indanes and indenes are among the most important carbocycles. Many indane and indene derivatives have shown important pharmacological activities, and the indane and indene nuclei are structural motifs present in several natural products of biological relevance. In spite of their importance, only a few reviews on their preparation methods have appeared so far in the literature, the most recent ones being published about ten years ago. The present Review is aimed at filling this gap, presenting some of the most important and innovative approaches to indanes and indenes that have been published in the course of the last ten years (coverage: from 2005 to May, 2015).

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“…1,4-Bis(propadienyl)benzene derivatives with varying functional groups (i.e. ester or ether functions) have been prepared by using propargylic carboxylates as substrates [208–209]. …”

Section: Reviewmentioning

confidence: 99%

The chemistry of bisallenes

Hopf¹,

Μαρκόπουλος²

2012

Beilstein J. Org. Chem.

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SummaryThis review describes the preparation, structural properties and the use of bisallenes in organic synthesis for the first time. All classes of compounds containing at least two allene moieties are considered, starting from simple conjugated bisallenes and ending with allenes in which the two cumulenic units are connected by complex polycyclic ring systems, heteroatoms and/or heteroatom-containing tethers. Preparatively the bisallenes are especially useful in isomerization and cycloaddition reactions of all kinds leading to the respective target molecules with high atom economy and often in high yield. Bisallenes are hence substrates for generating molecular complexity in a small number of steps (high step economy).

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Highly Regioselective Synthesis of Indene Derivatives Including an Allene Functional Group via Pd/C-Catalyzed Cyclization Reaction in Air

Cited by 56 publications

References 24 publications

Palladium-catalyzed construction of quaternary carbon centers with propargylic electrophiles

Palladium-catalyzed construction of quaternary carbon centers with propargylic electrophiles

Recent Advances in the Synthesis of Indanes and Indenes

The chemistry of bisallenes

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