Rh(iii)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C–H activation

Shi, Zhuangzhi; Boultadakis-Arapinis, Mélissa; Koester, Dennis C.; Glorius, Frank

doi:10.1039/c4cc00029c

Cited by 100 publications

(27 citation statements)

References 42 publications

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“… 13 As a temporary solution to this problem, our group and others have employed tethering strategies to increase the regioselectivity of the migratory insertion event (eqn 3). 14 , 15 Of course, regioselectivity controlled by the ligand on Rh would be the optimal solution to the selectivity problem (eqn 4). 16 Consequently, we focused our attention toward developing an intermolecular variant of this reaction that would provide product with improved regioselectivity.…”

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confidence: 99%

Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

2015

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We report the regioselective synthesis of dihydroisoquinolones from aliphatic alkenes and O-pivaloyl benzhydroxamic acids mediated by a Rh(III) precatalyst bearing sterically bulky substituents. While the prototypical Cp* ligand provides product with low selectivity, sterically bulky Cpt affords product with excellent regioselectivity for a range of benzhydroxamic acids and alkenes. Crystallographic evidence offers insight as to the source of the increased regioselectivity.

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confidence: 99%

Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

2015

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“…However, originally such oxidative Heck reactions were mostly limited to activated alkenes, such as acrylates and styrenes. Progressively, improved catalytic systems compatible now with unactivated alkane-substituted terminal olefins have been designed [70][71][72][73][74]. The key to success lies on a finely adjusted combination between a potent substrate (like naphthalene bearing O-methyl oxime or sulfonamide DGs) and reaction conditions, a design of a more potent, electron-deficient Cp*-derived Rh(III) catalyst, or performing intramolecular couplings.…”

Section: ð6þmentioning

confidence: 98%

Rh(III)- and Ir(III)-Catalyzed C–C Bond Cross Couplings from C–H Bonds

Wencel‐Delord

Patureau

Glorius

2015

C-H Bond Activation and Catalytic Functionalization I

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(M¼Ir, Rh) is formed and undergoes further transformations, according to the nature of the coupling partner, to finally afford a myriad of valuable, often complex, and otherwise difficult to access scaffolds like heterocycles and polyunsaturated skeletons. The major advances achieved in this field clearly showcase the potential of these catalysts to functionalize latent C-H bonds under surprisingly mild reaction conditions. The aim of this chapter is to present the latest and most representative contributions in the field of Rh(III)-and Ir(III)-catalyzed C-H activation by focusing on the reactivity of the corresponding metallacyclic intermediates.

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“…Notably, the less favoured C-H bond activated and functionalized under the reaction condition (Scheme 33). [52] The regioselectivity during the synthesis of the dihydroisoquinolinones by CÀ H functionalization of the aryl hydroxycarbamate using Rh(III) mainly depends on the substrates. Nicolai Cramer and co-workers developed the method for regioselective synthesis of the 3 and 4-substituted dihydroisoquinolinone where, the regioselectivity is controlled fully by the catalyst.…”

Section: Carbonylation/ Carbamoylation and Carbonyl Insertionmentioning

confidence: 99%

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

Kulkarni

Gaikwad

2020

ChemistrySelect

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The 3,4‐dihydroisoquinolin‐1(2H)‐one motifs found in many natural products, synthetic molecules with a diverse range of the biological activities and represent a privilege scaffold. Thereby the number of the innovative synthetic methodologies has been reported for constructions of this scaffold, which includes metal catalyzed and metal free method, multicomponent, domino one pot protocol, oxidation, Friedel‐Crafts type of cyclization. In the recent years many general protocols for the construction of this scaffold were reported in the literature and there is no focussed individual review for the 3,4‐dihydroisoquinolin‐1(2H)‐one since 2001. This review focuses on the reports describing the new method for the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one, published since 2001 to till date. In this review, we approach method of the synthesis of 3,4‐dihydroisoquinolin‐1(2H)‐one according to the strategy used for its synthesis, which includes, the intramolecular cyclization of carbamate/ urea/ thiourea/ isocyanate/ azidoamide, carbonylation/ carbomylation/ carbonyl insertion, metal catalyzed protocols by C−H activation by directing group, metal free domino procedures and oxidations of isoquinoline derivatives that were included in recent publications. Moreover, the reports published since 2001 for the synthesis of the chiral 3,4‐dihydroisoquinolin‐1(2H)‐one are included.

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Rh(iii)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C–H activation

Cited by 100 publications

References 42 publications

Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

Ligand design for Rh(iii)-catalyzed C–H activation: an unsymmetrical cyclopentadienyl group enables a regioselective synthesis of dihydroisoquinolones

Rh(III)- and Ir(III)-Catalyzed C–C Bond Cross Couplings from C–H Bonds

Recent Advances in Synthesis of 3,4‐Dihydroisoquinolin‐1(2H)‐one

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