Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines

Hampel, Nathalie; Zipse, Hendrik; Ofial, Armin R.

doi:10.1021/acs.orglett.5b02319

Cited by 22 publications

(9 citation statements)

References 94 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In order to reverse this selectivity, stabilised radical species must be formed to allow this selectivity change. In 2015, Ofial et al, have described an original sequential oxidative α-cyanation/ anti -Markovnikov hydroalkoxylation of tertiary allylamines catalysed by iron(II) chloride ( Scheme 11 ) [ 46 ]. The catalyst is involved in the first step of the transformation in which cyanide ion attacks the iminium functionality derived from the oxidation of the starting amine.…”

Section: Ironmentioning

confidence: 99%

First-Row Late Transition Metals for Catalytic Alkene Hydrofunctionalisation: Recent Advances in C-N, C-O and C-P Bond Formation

et al. 2017

View full text Add to dashboard Cite

This review provides an outline of the most noteworthy achievements in the area of C-N, C-O and C-P bond formation by hydroamination, hydroalkoxylation, hydrophosphination, hydrophosphonylation or hydrophosphinylation reaction on unactivated alkenes (including 1,2- and 1,3-dienes) promoted by first-row late transition metal catalytic systems based on manganese, iron, cobalt, nickel, copper and zinc. The relevant literature from 2009 until mid-2017 has been covered.

show abstract

Section: Ironmentioning

confidence: 99%

First-Row Late Transition Metals for Catalytic Alkene Hydrofunctionalisation: Recent Advances in C-N, C-O and C-P Bond Formation

et al. 2017

View full text Add to dashboard Cite

show abstract

“…In 2015, Ofial's group disclosed the iron-catalyzed oxidative α-cyanation at tertiary allyl amines. [31] The 14-19 h cyanation reaction of N,N-diallylaniline in presence of Me 3 SiCN and tBuOOH under N 2 at 23°C in methanol afforded the methanol addition product in good to excellent yields when FeCl 2 was used as the catalyst. The same reaction when carried out for 4 h resulted in 21% cyanated product without the formation of methanol addition product (Scheme 8).…”

Section: Cyanation Of Aminesmentioning

confidence: 99%

Recent Trends in the Iron‐Catalyzed Cyanation Reactions

Saranya¹,

Neetha²,

Aneeja³

et al. 2020

Adv Synth Catal

View full text Add to dashboard Cite

The review focuses on the iron-catalyzed cyanation reaction. This is the first review on this topic and covers literature till 2020 and comprehends all the works published in this field detailing the scope and limitations. The cyano compounds are important organic moiety and are widely used in synthetic organic chemistry; this review aims to help understand the various aspects of Fe-catalyzed cyanation reactions and its scope.

show abstract

“…In an interesting extension of this principle, allyl amines can undergo α-C-H cyanation in the presence of t BuOOH/FeCl 2 (typical conditions that allow α-C-H cyanation), but then subsequently undergo functionalization at the olefin. 26 Scheme 1. Previous α-C-H cyanation approaches and reported protocol.…”

Section: Introductionmentioning

confidence: 99%

Iron-Catalyzed α-C–H Cyanation of Simple and Complex Tertiary Amines

2021

View full text Add to dashboard Cite

This manuscript details the development of a general and mild protocol for the α-C-H cyanation of tertiary amines as well as its application in late stage functionalization. Suitable substrates include tertiary aliphatic, benzylic, and aniline-type substrates as well as complex substrates. Functional groups tolerated under the reaction conditions include various heterocycles, as well as ketones, amides, olefins, and alkynes. This broad substrate scope is remarkable, as comparable reaction protocols for α-C-H cyanation frequently occur via free radical mechanisms, and are thus fundamentally limited in their functional group tolerance. In contrast, the presented catalyst system tolerates functional groups that typically react with free radicals, suggesting an alternative reaction pathway. All components of the described system are readily available, allowing implementation of the presented methodology without the need for lengthy catalyst synthesis.Recent mechanistic work in the Fe catalyzed α-C-H oxidation of tertiary amines has uncovered a radical rebound ASSOCIATED CONTENT Supporting Information. Reaction optimization details, synthetic procedures, characterization for new and known compounds.

show abstract

Sequential Oxidative α-Cyanation/Anti-Markovnikov Hydroalkoxylation of Allylamines

Cited by 22 publications

References 94 publications

First-Row Late Transition Metals for Catalytic Alkene Hydrofunctionalisation: Recent Advances in C-N, C-O and C-P Bond Formation

First-Row Late Transition Metals for Catalytic Alkene Hydrofunctionalisation: Recent Advances in C-N, C-O and C-P Bond Formation

Recent Trends in the Iron‐Catalyzed Cyanation Reactions

Iron-Catalyzed α-C–H Cyanation of Simple and Complex Tertiary Amines

Contact Info

Product

Resources

About