Efficient solvent- and temperature-tuned access to aldoxime ethers and phenolic functions by Pd-catalyzed C–O cross-coupling of aldoximes with aryl bromides and bromo-chalcones

Reeta Reeta; T. M. Rangarajan; Kumar Kaushik; Rishi Pal Singh; Manjula Singh; Raj Pal Singh

doi:10.1039/c9nj05124d

Efficient solvent- and temperature-tuned access to aldoxime ethers and phenolic functions by Pd-catalyzed C–O cross-coupling of aldoximes with aryl bromides and bromo-chalcones

New Journal of Chemistry ◽

10.1039/c9nj05124d ◽

2020 ◽

Vol 44 (4) ◽

pp. 1326-1336 ◽

Cited By ~ 2

Author(s):

Reeta Reeta ◽

T. M. Rangarajan ◽

Kumar Kaushik ◽

Rishi Pal Singh ◽

Manjula Singh ◽

...

Keyword(s):

Cross Coupling ◽

Aryl Bromides ◽

Single Method ◽

First Time

A single method with a functionality switching option, to access oxime ethers and phenols, was developed for the first time for the Pd-catalyzed C–O cross-coupling of aryl bromides and bromo-chalcones with aldoximes.

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Enantioselective Reductive Diarylation of Alkenes by Ni-Catalyzed Domino Heck Cyclization/Cross Coupling

Synlett ◽

10.1055/s-0037-1612214 ◽

2019 ◽

Vol 30 (09) ◽

pp. 1008-1014 ◽

Cited By ~ 7

Author(s):

Kuai Wang ◽

Wangqing Kong

Keyword(s):

Functional Groups ◽

High Efficiency ◽

Cross Coupling ◽

Quaternary Centers ◽

Mild Conditions ◽

Rapid Access ◽

Heck Cyclization ◽

Aryl Bromides ◽

First Time ◽

Very High

A Ni-catalyzed enantioselective reductive diarylation of alkenes through a tandem Heck cyclization/cross coupling of two structurally distinguished aryl bromides is accomplished for the first time. This reaction takes place under very mild conditions with high efficiency and tolerates a variety of functional groups. Thus, it provides a rapid access to various medicinally relevant bis-heterocycles containing all-carbon quaternary centers with very high enantioselectivity.

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The Total Synthesis of Rhabdastrellic Acid A

10.26434/chemrxiv.7479944 ◽

2018 ◽

Author(s):

Yaroslav Boyko ◽

Christopher Huck ◽

David Sarlah

Keyword(s):

Total Synthesis ◽

Late Stage ◽

Cross Coupling ◽

Side Chains ◽

General Strategy ◽

Modular Approach ◽

Linear Sequence ◽

Generating Sequence ◽

First Time

<div>The first total synthesis of rhabdastrellic acid A, a highly cytotoxic isomalabaricane triterpenoid, has been accomplished in a linear sequence of 14 steps from commercial geranylacetone. The prominently strained <i>trans-syn-trans</i>-perhydrobenz[<i>e</i>]indene core characteristic of the isomalabaricanes is efficiently accessed in a selective manner for the first time through a rapid, complexity-generating sequence incorporating a reductive radical polyene cyclization, an unprecedented oxidative Rautenstrauch cycloisomerization, and umpolung 𝛼-substitution of a <i>p</i>-toluenesulfonylhydrazone with in situ reductive transposition. A late-stage cross-coupling in concert with a modular approach to polyunsaturated side chains renders this a general strategy for the synthesis of numerous family members of these synthetically challenging and hitherto inaccessible marine triterpenoids.</div>

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Monodentate Trialkylphosphines: Privileged Ligands in Metal-catalyzed Crosscoupling Reactions

Current Organic Chemistry ◽

10.2174/1385272824666200211114540 ◽

2020 ◽

Vol 24 (3) ◽

pp. 231-264 ◽

Cited By ~ 3

Author(s):

Kevin H. Shaughnessy

Keyword(s):

Transition Metal ◽

Cross Coupling ◽

Coupling Reactions ◽

Cross Coupling Reactions ◽

Aryl Bromides ◽

Wide Range ◽

Sterically Demanding ◽

Transition Metal Catalyzed ◽

Catalyzed Reactions ◽

Metal Catalyzed

Phosphines are widely used ligands in transition metal-catalyzed reactions. Arylphosphines, such as triphenylphosphine, were among the first phosphines to show broad utility in catalysis. Beginning in the late 1990s, sterically demanding and electronrich trialkylphosphines began to receive attention as supporting ligands. These ligands were found to be particularly effective at promoting oxidative addition in cross-coupling of aryl halides. With electron-rich, sterically demanding ligands, such as tri-tertbutylphosphine, coupling of aryl bromides could be achieved at room temperature. More importantly, the less reactive, but more broadly available, aryl chlorides became accessible substrates. Tri-tert-butylphosphine has become a privileged ligand that has found application in a wide range of late transition-metal catalyzed coupling reactions. This success has led to the use of numerous monodentate trialkylphosphines in cross-coupling reactions. This review will discuss the general properties and features of monodentate trialkylphosphines and their application in cross-coupling reactions of C–X and C–H bonds.

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Umpolung Coupling of Pyridine-2-carboxaldehydes and Propargylic Carbonates via N-Heterocyclic Carbene/Palladium Synergetic Catalysis

Chemical Communications ◽

10.1039/d1cc01311d ◽

2021 ◽

Author(s):

Weiyang Bi ◽

Yunhui Yang ◽

Song Ye ◽

Congyang Wang

Keyword(s):

Palladium Catalyst ◽

Coupling Reaction ◽

Cross Coupling ◽

Cooperative Catalysis ◽

Cross Coupling Reaction ◽

First Time

The umpolung cross-coupling reaction of pyridine-2-carboxaldehydes and propargylic carbonates has been developed for the first time through N-heterocyclic carbene/palladium cooperative catalysis with the judicious selections of the palladium catalyst, ligand...

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