Nickel‐Catalyzed Denitrogenative Annulation of 1,2,3‐Benzotriazin‐4‐(3<i>H</i>)‐ones with Benzynes for Construction of Phenanthridinone Scaffolds

Thorat, Vijaykumar H.; Upadhyay, Nitinkumar Satyadev; Murakami, Masahiro; Cheng, Chien‐Hong

doi:10.1002/adsc.201701143

Cited by 44 publications

(20 citation statements)

References 77 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…These triazole moieties, in the presence of nickel catalysts, readily react with suitable π‐components like alkyne, alkene, allene, aryne, isocyanide, and CO 2 to yield several heterocyclic compounds possessing biological applications. In continuation of our previous results, here we report a Ni‐catalyzed denitrogenative ortho‐ arylation of benzotriazinones with arylboronic acids and the application of this catalytic reaction.…”

Section: Introductionsupporting

confidence: 58%

Nickel‐Catalyzed Denitrogenative ortho‐Arylation of Benzotriazinones with Organic Boronic Acids: an Efficient Route to Losartan and Irbesartan Drug Molecules

2018

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Introductionsupporting

confidence: 58%

Nickel‐Catalyzed Denitrogenative ortho‐Arylation of Benzotriazinones with Organic Boronic Acids: an Efficient Route to Losartan and Irbesartan Drug Molecules

2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…With these requirements in mind, the denitrogenative annulation of benzotriazinones 35 was deemed an attractive reaction manifold. Such annulations have been demonstrated to be compatible with fluoride-mediated generation of transient species, such as arynes 36 . Furthermore, oxidative addition into benzotriazinones 12 is known to proceed rapidly and irreversibly to form metallacycle 14 (Fig.…”

mentioning

confidence: 99%

Intercepting fleeting cyclic allenes with asymmetric nickel catalysis

Yamano

Kelleghan

Shao

et al. 2020

Nature

View full text Add to dashboard Cite

Strained cyclic organic molecules, such as arynes, cyclic alkynes and cyclic allenes, have intrigued chemists for more than a century with their unusual structures and high chemical reactivity 1 . The considerable ring strain (30-50 kilocalories per mole) 2,3 that characterizes these transient intermediates imparts high reactivity in many reactions, including cycloadditions and nucleophilic trappings, often generating structurally complex products 4 . Although strategies to control absolute stereochemistry in these reactions have been reported using stoichiometric chiral reagents 5,6 , catalytic asymmetric variants to generate enantioenriched products have remained difficult to achieve. Here we report the interception of racemic cyclic allene intermediates in a catalytic asymmetric reaction and provide evidence for two distinct mechanisms that control absolute stereochemistry in such transformations: kinetic differentiation of allene enantiomers and desymmetrization of intermediate π-allylnickel complexes. Computational studies implicate a catalytic mechanism involving initial kinetic differentiation of the cyclic allene enantiomers through stereoselective olefin insertion, loss of the resultant stereochemical information, and subsequent introduction of absolute stereochemistry through desymmetrization of an intermediate π-allylnickel complex. These results reveal reactivity that is available to cyclic allenes beyond the traditional cycloadditions and nucleophilic trappings previously reported, thus expanding the types of product accessible from this class of intermediates. Additionally, our computational studies suggest two potential strategies for stereocontrol in reactions of cyclic allenes. Combined, these results lay the foundation for the development of catalytic asymmetric reactions involving these classically avoided strained intermediates.

show abstract

“…A Ni-catalyzed denitrogenative cascade annulation method for the synthesis of phenanthridinone scaffolds was demonstrated by Cheng and co-workers ( Scheme 45 ). 59 The report involved treatment of benzotriazin-4-(3 H )-ones 12 with 2-(trimethylsilyl)aryl triflates 64a in the presence of 10 mol% Ni(cod) 2 , 20 mol% dppm, and 3 equiv. of KF as the fluoride source to generate the corresponding phenanthridinone scaffolds 13 in good yield.…”

Section: Carboamination Of Alkynesmentioning

confidence: 99%

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

Nanda

Mallik

2022

RSC Adv.

View full text Add to dashboard Cite

show abstract

Nickel‐Catalyzed Denitrogenative Annulation of 1,2,3‐Benzotriazin‐4‐(3H)‐ones with Benzynes for Construction of Phenanthridinone Scaffolds

Cited by 44 publications

References 77 publications

Nickel‐Catalyzed Denitrogenative ortho‐Arylation of Benzotriazinones with Organic Boronic Acids: an Efficient Route to Losartan and Irbesartan Drug Molecules

Nickel‐Catalyzed Denitrogenative ortho‐Arylation of Benzotriazinones with Organic Boronic Acids: an Efficient Route to Losartan and Irbesartan Drug Molecules

Intercepting fleeting cyclic allenes with asymmetric nickel catalysis

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

Contact Info

Product

Resources

About