An <i>anti</i>-Carbopalladation/Amination Cascade with Alkynes: Access to Tetrasubstituted Enamines and Pyrroles

Schitter, Theresa; Stammwitz, Simon; Jones, Peter G.; Werz, Daniel B.

doi:10.1021/acs.orglett.9b03625

Cited by 29 publications

(6 citation statements)

References 63 publications

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“… Noncovalent Se···O interactions were revealed in the X-ray structure analysis of the products. The same group has also reported the efficient Pd-catalyzed cyanosulfenylation of alkynes, leading to substituted thienol ethers, and developed a powerful synthetic concept. − …”

Section: Catalytic Z–z and C–z Bond Addition Reactions (Z = S Se Te)mentioning

confidence: 99%

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

2022

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In the present review, we discuss recent progress in the field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are consideredcatalytic cross-coupling reactions and catalytic addition reactions. The development of advanced catalytic systems is aimed at improved catalyst efficiency, reduced catalyst loading, better cost efficiency, environmental concerns, and higher selectivity and yields. The important rise of research efforts in sustainability and green chemistry areas is critically assessed. The paramount role of mechanistic studies in the development of a new generation of catalytic systems is addressed, and the key achievements, problems, and challenges are summarized for this field.

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Section: Catalytic Z–z and C–z Bond Addition Reactions (Z = S Se Te)mentioning

confidence: 99%

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

2022

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“…carboamination for the diastereoselective synthesis of tetrasubstituted enamines and pyrroles ( Scheme 56 ). 69 They chose propargyl amine-tethered bromobenzenes 92 as suitable precursors, which upon treatment with PdCl 2 (PhCN) 2 (5 mol%), [ t Bu 3 PH][BF 4 ] (10 mol%) and 5 equivalents of K 3 PO 4 as the base, afforded tetrasubstituted amines 93 as the sole product in excellent yield. On the other hand, the use of 5 mol% Pd(dba) 2 and 5 equivalents of Et 3 N as the base delivered pyrroles 94 as the sole product.…”

Section: Intramolecular Carboaminationmentioning

confidence: 99%

1,2-Difunctionalizations of alkynes entailing concomitant C–C and C–N bond-forming carboamination reactions

Nanda

Mallik

2022

RSC Adv.

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“…Werz demonstrated the use of PdCl 2 (PhCN) 2 catalyst in the synthesis of substituted pyrroles 59 from internal alkynes 58 (Scheme 7). 47 The mechanism of this reaction commences with oxidative addition of the aryl bromide moiety into the Pd(0) source, leading to a syn-migratory insertion into the alkyne C≡C bond to form Pd-vinyl species 60. This is followed by alkene isomerization to 62 via syn-anti transition state 61 and coordination of the amine to the palladium resulting in reductive elimination of intermediate 63.…”

Section: Review Synthesismentioning

confidence: 99%

Recent Advancements in Pyrrole Synthesis

Philkhana¹,

Badmus²,

Reis³

et al. 2021

Synthesis

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This review article features selected examples on the synthesis of functionalized pyrroles that were reported between 2014 and 2019. Pyrrole is an important nitrogen-containing aromatic heterocycle that can be found in numerous compounds of biological and material significance. Given its vast importance, pyrrole continues to be an attractive target for the development of new synthetic reactions. The contents of this article are organized by the starting materials, which can be broadly classified into four different types: substrates bearing π-systems, substrates bearing carbonyl and other polar groups, and substrates bearing heterocyclic motifs. Brief discussions on plausible reaction mechanisms for most transformations are also presented.1 Introduction2 From π-Systems2.1 Alkenes2.2 1,6-Dienes2.3 Allenes2.4 Alkynes2.5 Propargylic Groups2.6 Homopropargylic Amines3 From Carbonyl Compounds3.1 Aldehydes3.2 Ketones3.3 Cyanides and Isocyanides3.4 Formamides3.5 β-Enamines3.6 Dicarbonyl Compounds4 From Polar Compounds4.1 Aminols4.2 Diols4.3 Organonitro Compounds5 From Heterocycles5.1 Münchnones5.2 Isoxazoles5.3 Carbohydrates5.4 trans-4-Hydroxy-l-prolines5.5 Pyrrolines6 Summary

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An anti-Carbopalladation/Amination Cascade with Alkynes: Access to Tetrasubstituted Enamines and Pyrroles

Cited by 29 publications

References 63 publications

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

1,2-Difunctionalizations of alkynes entailing concomitant C–C and C–N bond-forming carboamination reactions

Recent Advancements in Pyrrole Synthesis

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