Reductive cleavage of resin bound arylsulfonates

Jin, Sun; Holub, David P.; Wustrow, David

doi:10.1016/s0040-4039(98)00640-6

Cited by 37 publications

(18 citation statements)

References 25 publications

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“…Selenium linker (Nicolaou, Ruhland): The selenium ± carbon bond is prone, owing to its weakness, to undergo homolytic cleavage to give radicals. [14] It might be anticipated that this type of linker is also suitable for functionalization (see below). [13a] Recently Nicolaou et al [13b] and Ruhland et al [13c] independently developed more efficient methods for the preparation of selenium-containing supports in their development of traceless linkers.…”

Section: Silicon (Ellman and Veber) And Germanium (Ellman) Linkersmentioning

confidence: 99%

Traceless Linkers-Only Disappearing Links in Solid-Phase Organic Synthesis?

Bräse

Dahmen

2000

Chem. Eur. J.

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Traceless linkers, which enable the attachment of arenes and alkanes to a polymeric support, have received increased attention in recent years. These anchoring groups allow chemical transformations on the polymer-bound molecules, which can be cleaved from the resin leaving no residual functionality to bias the library. Various approaches based on different Group 14 to Group 16 heteroatoms have been developed in the past and used in new syntheses of diverse compound libraries.

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Section: Silicon (Ellman and Veber) And Germanium (Ellman) Linkersmentioning

confidence: 99%

Traceless Linkers-Only Disappearing Links in Solid-Phase Organic Synthesis?

Bräse

Dahmen

2000

Chem. Eur. J.

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“…However, the discovery that they are viable substrates for cross-coupling reactions has been exploited in multifunctional cleavage approaches (48)(49)(50). Similarly, aryl perfluoroalkane sulfonate (PFS) esters are widely used as substrates for cross-coupling reactions and PFS linker units, which exploit this, have also been developed by Pan and Holmes.…”

Section: Diversity Is Incorporated By Other Methodsmentioning

confidence: 99%

Solid‐Phase Organic Synthesis

Fawaz

Scott

2014

Kirk-Othmer Encyclopedia of Chemical Technology

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Solid‐phase organic synthesis (SPOS), a synthetic technique in which reaction components (eg, substrates, catalysts, and reagents) are attached to insoluble polymer supports, was introduced by Prof. Robert Bruce Merrifield in the 1960s. In the decades since its introduction, SPOS has matured into a powerful technique with applications in, for example, the synthesis of small molecules, drugs and natural products, asymmetric synthesis, and organometallic chemistry. In addition, the ease with which many SPOS reactions can be automated and run in parallel means it has a pivotal role in library synthesis for combinatorial chemistry and diversity‐oriented synthesis. This article introduces the principles of SPOS and highlights key concepts including linker units, SPOS reactions, immobilized catalysts, and solid‐supported reagents through literature examples.

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“…Replacement of silicon with the less acid-stable germanium derivative, [15i,j] though rather expensive, is one solution to this problem. Another solution, however, is offered by Wustrow and co-workers (Table 5 entry 2): [16] The aryl sulfonate system undergoes efficient Pd(0)-catalyzed reductive cleavage with electron-poor arenes.…”

Section: Pact Hàcsp 2 (Arene) Linkersmentioning

confidence: 99%