Polyaromatic Ribbon/Benzofuran Fusion via Consecutive Endo Cyclizations of Enediynes

Byers, Philip M.; Rashid, Julian I.; Mohamed, Rana K.; Alabugin, Igor V.

doi:10.1021/ol302922t

Cited by 92 publications

(45 citation statements)

References 44 publications

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“…This cyclization mode has been shown to be effective in initiating an all endo‐selective cascade, which fuses a polycyclic aromatic backbone to the electron‐rich furan subunit, as shown in Scheme .…”

Section: Extension 4: Promoted Cyclizationsmentioning

confidence: 99%

The Baldwin rules: revised and extended

Gilmore

Mohamed

Alabugin

2016

WIREs Comput Mol Sci

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122

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The Baldwin rules constitute one of the clearest examples of the success which can be obtained through the application of stereoelectronic concepts to reaction design. With thousands of examples, the predictive power of these rules is inarguable. However, time has revealed a number of exceptions and gray areas within these rules, leading to extensions and revisions. In this review, we will present an overview of how subsequent studies of ring closure have clashed with several of Baldwin's predictions, leading to the revision of some classes of ring closure (alkyne cyclizations, electrophilic closures, etc.). We also discuss for which the original rules were vague (epoxides) or absent (promoted cyclizations), and the evidence revealed since Baldwin's work that has allowed for a better understanding of these ambiguities. With the concise summation of these amendments, this review aims to present an overview of the understanding of cyclization reactions to date. For further resources related to this article, please visit the WIREs website

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Section: Extension 4: Promoted Cyclizationsmentioning

confidence: 99%

The Baldwin rules: revised and extended

Gilmore

Mohamed

Alabugin

2016

WIREs Comput Mol Sci

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122

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“…As a continuation of our work on cascade alkyne cyclizations,39,79 we reported that the Au‐catalyzed cyclizations of enediynes can be used for the development of “all endo ‐selective” cascades,80 which are complementary to the “all‐ exo ” radical transformations of tri‐ and tetraalkynes39,81 developed according to the revised rules for alkyne cyclization reactions36 (Scheme ).…”

Section: Masked Zwitterions and Carbenes In Transition‐metal‐catalmentioning

confidence: 99%

How to Lose a Bond in Two Ways ― The Diradical/Zwitterion Dichotomy in Cycloaromatization Reactions

2013

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Cycloaromatization reactions decouple two electrons by breaking two π bonds to form only one σ bond and illustrate one of the most common mechanistic dichotomies in chemistry, namely the two ways of breaking a chemical bond: Zwitterionic or diradical. With a suitable choice of reaction conditions, substitution patterns, and catalysts, cycloaromatization processes can be redirected from the usual formation of a diradical towards a variety of zwitterionic pathways. This review illustrates the practical approaches for directing zwitterionic cycloaromatization reactions and lays the mechanistic foundations for the further development of this emerging field.

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“…Alabugin and co workers reported the synthesis of benzofuran fused chrysene derivative 21 based on the Sonogashira coupling followed by furan formation from triyne 20 with 2 iodophenol 19 and subsequent gold catalyzed biscyclization. 16 Quite recently, interesting regioselectivity in the gold catalyzed hydroarylation was observed by Wang et al 17 They used benzoic acid derived diynes 22 bearing a terminal alkyne moiety and obtained the biscyclization products 23. They proposed a mechanism that involves activation of the terminal alkyne by the cationic gold complex to promote a 5 exo dig cyclization, which is followed by nucleophilic attack of the carboxy group.…”

Section: Synthesis Of Benzo[a]naphtho[21 C]carbazoles and Related Comentioning

confidence: 99%

Gold-Catalyzed Atom-Economical Cascade Reactions of Alkynes for Ring Formation

Ohno¹,

Oishi²,

Fujii³

2014

J. Synth. Org. Chem. Jpn.

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Abstract:The development of cascade reactions is an area of considerable interest in modern organic chemistry. Recent advances in homogeneous gold catalysis have opened up further possibilities for atom economical cascade reactions for ef cient synthesis of complex target molecules. We have been involved in the development of cascade reactions based on the activation of carbon carbon triple bonds by a gold catalyst to facilitate intra and intermolecular nucleophilic attack. Quite recently, we succeeded in forming gold carbenoids, which are useful intermediates for further elaborations, from ynamides. This account describes our efforts towards the development of gold catalyzed cascade reactions for atom economical synthesis of fused carbazoles, naphthalenes, dihydropyrazoles/indazoles, and indoloquinolines. Scheme 1. Classi cation of gold catalyzed cascade cyclization of alkynes.

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Polyaromatic Ribbon/Benzofuran Fusion via Consecutive Endo Cyclizations of Enediynes

Cited by 92 publications

References 44 publications

The Baldwin rules: revised and extended

The Baldwin rules: revised and extended

How to Lose a Bond in Two Ways ― The Diradical/Zwitterion Dichotomy in Cycloaromatization Reactions

Gold-Catalyzed Atom-Economical Cascade Reactions of Alkynes for Ring Formation

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