Synthesis of Highly Functionalised Dihydrobenzofurans and Indolines by Palladium‐Catalysed Mizoroki–Heck–Heteroannulation Cascade Reactions of Alkoxy‐1,3‐dienes

Toppino, Antonio; Arru, Paolo; Bianco, Niccolò; Prandi, Cristina; Venturello, Paolo; Deagostino, Annamaria

doi:10.1002/ejoc.201300972

Cited by 8 publications

(2 citation statements)

References 42 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Arylbutadienes with either electron-withdrawing or -donating substituents were all tolerated in this protocol, such as cyclohexyl-and diphenyl-substituted buta-1,3-dienes. N-Protected 2-iodoanilines 41 were also useful nucleophiles for cascade reaction with 1-alkoxydienes 42 affording 2-vinylindolines 43 (Scheme 14) 17 The addition of the aryl-Pd(II) complex to the diene moiety leads to a -allyl-Pd intermediate, which undergoes intramolecular nucleophilic substitution by the nitrogen atom to afford products 43. The high regioselective outcome was due to steric factors.…”

Section: Scheme 12mentioning

confidence: 99%

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

et al. 2020

View full text Add to dashboard Cite

Palladium-catalyzed domino reactions are advanced tools in achieving various nitrogen-containing heterocycles in an efficient and economical manner due to the reduced number of steps in the process. This review highlights recent advances in domino processes aimed at the synthesis of indole derivatives and polycyclic systems containing the indole nucleus in intra/intra- or intra/intermolecular reactions. In particular, we consider domino processes that involve a double bond in a step of the sequence, which allow the issue of regioselectivity in the cyclization to be faced and overcome. The different sections in this review focus on the synthesis of the indole nucleus and functionalization of the scaffold starting from different substrates that have been identified as activated starting materials, which involve a halogenated moiety or unactivated unsaturated systems. In the former case, the reaction is under Pd(0) catalysis, and in the second case a Pd(II) catalytic species is required and then an oxidant is necessary to reconvert the Pd(0) into the active Pd(II) species. On the other hand, the second method has the advantage that it uses easy available and inexpensive substrates.1 Introduction2 Indole Scaffold Synthesis2.1 Activated Substrates2.2 Unactivated Substrates3 Functionalization of Indole Scaffold3.1 Activated Substrates3.2 Unactivated Substrates4 Conclusions

show abstract

Section: Scheme 12mentioning

confidence: 99%

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

et al. 2020

View full text Add to dashboard Cite

show abstract

“…These alkenylmetal intermediates are generally prepared in situ through the reaction of alkenylhalides with a stoichiometric amount or an excess of metallic reagents (Mg, Li, Cu, and Zn), − or with Cr catalysts under reductive conditions, or through alkyne hydrometalation with metallic hydrides. , In recent years, many synthetic strategies that avoid the use of discrete metalloalkenes have been reported: metal-catalyzed alkene-carbonyl and alkyne–carbonyl reductive coupling, in addition to the redox-neutral alternative between alcohols and alkynes using Ru, Os, and Ni catalysts . In our laboratory, for several years, we have been studying the reactivity of alkoxy-π-allyl Pd(II) complexes in domino Heck reactions − for the preparation of highly functionalized molecules. Recently, considering their chemical versatility, especially in Pd(0) cross-couplings, − we exploited N -tosylhydrazones as nucleophilic partners for the selective synthesis of conjugated and skipped dienes .…”

mentioning

confidence: 99%

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji–Trost-Like “Palladium–Iodide” Catalyzed Coupling

Parisotto

Deagostino

2018

Org. Lett.

Self Cite

View full text Add to dashboard Cite

An unprecedented efficient palladium(0)-catalyzed reaction of vinyl oxiranes with N-tosylhydrazones, affording "skipped" allylic alcohols in total regioselectivity and stereoselectivity, with excellent functional-group compatibility, is reported. In this Tsuji−Trost-like allylation, we propose the use of N-tosylhydrazones as a synthetic equivalent of α-styryl anions. More than 20 new products are described, including naturally occurring derivatives. A catalytic system involving an iodide (I − ) source is necessary to sustain the catalytic cycle.

show abstract

Palladium(II) acetate

Ho¹,

Fieser²,

Danheiser³

et al. 2017

Fieser and Fieser's Reagents for Organic Synthesis

View full text Add to dashboard Cite

Synthesis of Highly Functionalised Dihydrobenzofurans and Indolines by Palladium‐Catalysed Mizoroki–Heck–Heteroannulation Cascade Reactions of Alkoxy‐1,3‐dienes

Abstract: A Mizoroki–Heck–heteroannulation cascade reaction has been used to prepare substituted dihydrobenzofurans and indolines in good yields by the reaction between functionalised alkoxy‐1,3‐dienes and several o‐iodophenols or protected o‐iodoanilines.

Cited by 8 publications

References 42 publications

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

Pd-Catalyzed Domino Reactions Involving Alkenes To Access Substituted Indole Derivatives

Synthesis of Highly Functionalized Allylic Alcohols from Vinyl Oxiranes and N-Tosylhydrazones via a Tsuji–Trost-Like “Palladium–Iodide” Catalyzed Coupling

Palladium(II) acetate

Contact Info

Product

Resources

About