Rhodium(III)‐Catalyzed Dehydrogenative Heck Reaction of Salicylaldehydes

Shi, Zhuangzhi; Schröder, Nils; Glorius, Frank

doi:10.1002/anie.201203224

Cited by 163 publications

(58 citation statements)

References 101 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[11][12][13] Along with this line of research, we became interested in the ability of aCo I catalyst to effect activation and transformation of SA. Theuse of Mn or In as an alternative reductant resulted in al ower yield of 3aa (entries 7,8). Both the reactions commonly feature the expense of another molecule of SA as an acceptor of the aldehyde hydrogen presumably through a C À Ho xidative addition/C = Oh ydrometalation sequence, while the latter reaction involves the action of Zn as as toichiometric reductant.…”

Section: Junfeng Yang and Naohiko Yoshikai*mentioning

confidence: 99%

Cobalt‐Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4‐Chromanones

Yang

Yoshikai

2016

Angew Chem Int Ed

View full text Add to dashboard Cite

A unique cobalt(I)-diphosphine catalytic system has been identified for the coupling of salicylaldehyde (SA) and an internal alkyne affording a dehydrogenative annulation product (chromone) or a reductive annulation product (4-chromanone) depending on the alkyne substituents. Distinct from related rhodium(I)- and rhodium(III)-catalyzed reactions of SA and alkynes, these annulation reactions feature aldehyde C-H oxidative addition of SA and subsequent hydrometalation of the C=O bond of another SA molecule as common key steps. The reductive annulation to 4-chromanones also involves the action of Zn as a stoichiometric reductant. In addition to these mechanistic features, the Co(I) catalysis described herein is complementary to the Rh(I) - and Rh(III) -catalyzed reactions of SA and internal alkynes, particularly in the context of chromone synthesis.

show abstract

Section: Junfeng Yang and Naohiko Yoshikai*mentioning

confidence: 99%

Cobalt‐Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4‐Chromanones

Yang

Yoshikai

2016

Angew Chem Int Ed

View full text Add to dashboard Cite

show abstract

“…A Rh(III)-catalyzed dehydrogenative Heck reaction of salicylaldehydes bearing various functional groups with olefins was reported by Glorius and coworkers (Scheme 6.7) [16]. Among the electron-deficient alkenes investigated, ethyl acrylates exhibited optimal activity to give the corresponding products in good yields.…”

Section: Other Five-membered Oxygen-containing Heterocyclesmentioning

confidence: 99%

“…The Glorius group [16] 44% yield (Scheme 6.23b). While chromane 88 was obtained in 34% yield in the presence of 2.0 equiv.…”

Section: Chromonesmentioning

confidence: 99%

Rh‐Catalyzed Synthesis of Oxygen‐Containing Heterocycles

Liu

Shi

2016

Transition Metal‐Catalyzed Heterocycle Synthesis via CH Activation

View full text Add to dashboard Cite

“…Towards this goal, we envisioned that the O-NHAc (oxyacetamide) fulfills the multifunctional criteria of such a group due to its excellent metal directing ability, the oxidative O-N bonds and nucleophilic amide functionality [11][12][13][14] . We chose the rhodium catalysed C-H vinylation reaction between an N-aryloxyacetamide and an internal alkyne to explore the cascade strategy [17][18][19] . After the C-H vinylation, the oxyacetamide DG might undergo transitionmetal-catalysed dioxygenation reaction to give rise to a fused dihydrofuran-dihydrooxazole scaffold.…”

mentioning

confidence: 99%

A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades

et al. 2014

View full text Add to dashboard Cite

The C-H activation strategy has become one of the preferred methods to introduce chemical functionality to a chemically inert carbon atom. Intensive efforts have been devoted to developing either versatile bond formations (product structural diversity) or effective directing groups (substrate site selectivity). From the views of medicinal and synthetic practitioners, the C-H activation approach remains inadequate due to its limitation to pointto-point derivatization. Direct assembly of 3D molecular complexity in a single step remains elusive for this strategy. Towards this goal, a multitasking functional group is required to accomplish several missions in one pot: site selecitivity, cleavability and redox versatility. We demonstrate that an oxyacetamide group is such a multifunctional warhead that enables a series of C-H functionalization cascades and allows direct access to structurally diverse polycyclic heterocyles in one pot. The progress of these reaction cascades were fully controlled by oxidants and temperature. The proliferation of the reaction chain can be extended to a four-step cascade.

show abstract

Rhodium(III)‐Catalyzed Dehydrogenative Heck Reaction of Salicylaldehydes

Cited by 163 publications

References 101 publications

Cobalt‐Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4‐Chromanones

Cobalt‐Catalyzed Annulation of Salicylaldehydes and Alkynes to Form Chromones and 4‐Chromanones

Rh‐Catalyzed Synthesis of Oxygen‐Containing Heterocycles

A multitasking functional group leads to structural diversity using designer C–H activation reaction cascades

Contact Info

Product

Resources

About