Annelated Cyclobutanes by Fe‐Catalyzed Cycloisomerization of Enyne Acetates

Kramm, Frederik; Teske, Johannes; Ullwer, Franziska; Frey, Wolfgang; Plietker, Bernd

doi:10.1002/anie.201806693

Cited by 14 publications

(11 citation statements)

References 42 publications

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“…1 b was synthesized in two steps according to the described in the literature procedure. [44] N-propargylamine (7.69 mL, 120 mmol, 1.00 eq.) was dissolved in dichloromethane (285 mL).…”

Section: Synthesis Of N-allyl-4-methyl-n-(prop-2-yn-1-yl)benzenesulfo...mentioning

confidence: 99%

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

et al. 2022

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Dedicated to Professor Rinaldo Poli on the occasion of his 65th birthday.We describe the use of CO 2 as a promising C1 source instead of CO in the tandem Pauson-Khand reaction. The reaction is achieved by combining the reduction of CO 2 to CO using a metal organic framework (MOF) catalyst with homogeneous rhodium catalysts for the cycloaddition step. A range of substrates were converted in moderate to good yields.

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“…1 b was synthesized in two steps according to the described in the literature procedure. [44] N-propargylamine (7.69 mL, 120 mmol, 1.00 eq.) was dissolved in dichloromethane (285 mL).…”

Section: Synthesis Of N-allyl-4-methyl-n-(prop-2-yn-1-yl)benzenesulfo...mentioning

confidence: 99%

Tandem Pauson‐Khand Reaction Using Carbon Dioxide as the C1‐Source

et al. 2022

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“…Due to this restriction, photochemical [2 + 2] cycloaddition between two olefins is the most common strategy to form cyclobutanes. In 2018, the group of Plietker reported an unusual cycloisomerization of enynes using a cationic iron nitrosyl catalyst (Scheme 24) [61]. Their 1,6-and 1,7-enyneacetates were expected to isomerize to allenes, but instead isomerized to their corresponding bicyclo [3.…”

Section: Isomerizationsmentioning

confidence: 99%

“…catalyst (Scheme 24)[61]. Their 1,6-and 1,7-enyneacetates were expected to isomerize to allenes, but…”

mentioning

confidence: 99%

On the Use of Iron in Organic Chemistry

Guðmundsson

Bäckvall

2020

Molecules

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Transition metal catalysis in modern organic synthesis has largely focused on noble transition metals like palladium, platinum and ruthenium. The toxicity and low abundance of these metals, however, has led to a rising focus on the development of the more sustainable base metals like iron, copper and nickel for use in catalysis. Iron is a particularly good candidate for this purpose due to its abundance, wide redox potential range, and the ease with which its properties can be tuned through the exploitation of its multiple oxidation states, electron spin states and redox potential. This is a fact made clear by all life on Earth, where iron is used as a cornerstone in the chemistry of living processes. In this mini review, we report on the general advancements in the field of iron catalysis in organic chemistry covering addition reactions, C-H activation, cross-coupling reactions, cycloadditions, isomerization and redox reactions.

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“…In 2016, Sheldrake demonstrated that aldehyde 14 reacted with diethylamine at room temperature using K 2 CO 3 as a base to form the bicyclic alkene 15 . Finally, in 2018, Plietker and co-workers developed a cyclization of substrates 16 in the presence of iron catalyst 17 into bicyclic products of type 18 …”

Section: Introductionmentioning

confidence: 98%