Lewis Acid Catalyzed Intermolecular Olefin Hydroamination: Scope, Limitation, and Mechanism

Cheng, Xiaojuan; Xia, Yuanzhi; Wei, Han‐Xun; Xu, Bin; Zhang, Chongguang; Li, Yahong; Qian, Guimin; Zhang, Xiaohua; Li, Kai; Li, Wu

doi:10.1002/ejoc.200701080

Cited by 59 publications

(24 citation statements)

References 77 publications

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“…Preliminary investigations in the field have brought into light the benefit of iron(III) salts as Lewis acid catalysts for the C-N bond formation by the addition of electronically deficient amines, mainly as N -tosylamines, onto unactivated alkenes via a hydroamidation process [ 25 , 26 , 27 , 28 , 29 ]. However, these early studies are limited to electronically biased amines and problems of regioselectivity have been noticed in some cases [ 25 ].…”

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

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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.

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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

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“…The first involves the alkylation of the starting aniline with the inexpensive 3,3-dimethylallyl bromide/chloride, followed by cyclisation mediated by Lewis acids, or under acidic conditions [5–6]. A second, analogous approach involves an initial acylation with the commercially available 3,3-dimethylacryloyl chloride, followed by Friedel–Crafts cyclisations that also use Lewis acids [7].…”

Section: Introductionmentioning

confidence: 99%

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Chisholm¹,

Zhou²,

Pohl³

et al. 2016

Beilstein J. Org. Chem.

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SummaryThe synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.

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“…Li studied the efficiency of a number of Lewis acids, including FeCl 3 , BiCl 3 , ZrCl 4 and AlCl 3 , for the addition of aniline derivatives 14 to norbornene (12, Scheme 7). [22] BiCl 3 gave the highest yields for the widest range of aniline derivatives; however, a mixture of products 15 and 16 arising from hydroamination and hydroarylation were obtained. By comparison, FeCl 3 catalysed the reaction with excellent selectivity for hydroamination, although only aniline derivatives bearing electron-withdrawing groups gave hydroamination products 15 in high yields.…”

Section: Addition Of N O and S Nucleophiles To Alkenes And Alkynesmentioning

confidence: 82%

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

2014

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The metal‐catalysed hydrofunctionalisation of alkenes and alkynes provides a convenient and atom‐economic route to diversely functionalised products with control of regio‐, chemo‐ and stereoselectivity. As one of the most abundant elements on earth, iron offers a level of sustainable and long‐term availability that is uncommon for most transition metals. Although iron is commonly found in the oxidation states of +2 and +3, the use of redox‐active ligands has allowed the synthesis and application of low oxidation state iron complexes in catalysis. A broad range of hydrofunctionalisation reactions have been developed by using iron catalysts in a wide variety of oxidation states. Intense development over the past decade has resulted in the development of iron‐catalysed hydroamination, hydroalkoxylation, hydrocarboxylation, hydrothiolation, hydrovinylation, hydrosilylation, hydroboration, hydrophosphination, hydromagnesiation and carbonylation reactions, amongst others. With the field still in its infancy, there is great potential for further developments in the mechanistic understanding and synthetic and industrial applicability of these processes.

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Lewis Acid Catalyzed Intermolecular Olefin Hydroamination: Scope, Limitation, and Mechanism

Cited by 59 publications

References 77 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

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

Iron‐Catalysed Hydrofunctionalisation of Alkenes and Alkynes

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