Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(<scp>i</scp>)/Pd(0)/Cu(<scp>ii</scp>) cascade catalysis of 2-iodoaniline/phenols

Seath, Ciaran P.; Wilson, Kirsty L.; Campbell, Angus; Mowat, Jenna M.; Watson, Allan J. B.

doi:10.1039/c6cc04554e

Cited by 26 publications

(13 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…158 Watson has also developed a synthesis of 2-borylated indoles/benzofurans involving a palladium catalyzed cascade reaction with ethynyl BMIDA and 2-iodoanilines. 159 Similarly, borylated indolenes and benzofurans have been synthesized through gold-catalyzed intramolecular cyclizations onto alkynes. 160 These reactions are expanding the collection of MIDA boronate building blocks available for small molecule construction, and hundreds of MIDA boronates are already commercially available.…”

Section: Advances Towards a General Platform For Iterative Small Molementioning

confidence: 99%

Towards the generalized iterative synthesis of small molecules

2018

View full text Add to dashboard Cite

Small molecules have extensive untapped potential to benefit society, but access to this potential is too often restricted by limitations inherent to the customized approach currently used to synthesize this class of chemical matter. In contrast, the “building block approach”, i.e., generalized iterative assembly of interchangeable parts, has now proven to be a highly efficient and flexible way to construct things ranging all the way from skyscrapers to macromolecules to artificial intelligence algorithms. The structural redundancy found in many small molecules suggests that they possess a similar capacity for generalized building block-based construction. It is also encouraging that many customized iterative synthesis methods have been developed that improve access to specific classes of small molecules. There has also been substantial recent progress toward the iterative assembly of many different types of small molecules, including complex natural products, pharmaceuticals, biological probes, and materials, using common building blocks and coupling chemistry. Collectively, these advances suggest that a generalized building block approach for small molecule synthesis may be within reach.

show abstract

Section: Advances Towards a General Platform For Iterative Small Molementioning

confidence: 99%

Towards the generalized iterative synthesis of small molecules

2018

View full text Add to dashboard Cite

show abstract

“…Specifically, employing ortho -amino ( 5 ) or ortho -hydroxyaryl iodides ( 6 ) in the Sonogashira process generated an alkyne intermediate that, upon increasing the reaction temperature from 30 °C to 60 °C, could undergo 5- endo -dig cyclisation to forge functionalised and pharmaceutically relevant indole, benzofuran, and aza-indole scaffolds in a single operation ( 7a – f ) [48–52]. …”

Section: Resultsmentioning

confidence: 99%

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Wilson¹,

Kennedy²,

Murray³

et al. 2016

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummaryPd-catalysed C–C bond formation is an essential tool within the pharmaceutical and agrochemical industries. Many of these reactions rely heavily on polar aprotic solvents; however, despite their utility, these solvents are incompatible with the drive towards more sustainable chemical synthesis. Herein, we describe the scope and limitations of an alternative to DMF derived from renewable sources (CyreneTM) in Sonogashira cross-coupling and Cacchi-type annulations.

show abstract

“…This complexation facilitates the addition of nitrogen to the triple bond. The synthesis of regioisomeric 2-indolylboronates is also feasible [110], although a procedure starting from 2-iodoanilines and MIDAB-acetylene under typical Miyaura borylation conditions would have to be used.…”

Section: Synthetic Approaches To Indolylboronic Acidsmentioning

confidence: 99%

Indolylboronic Acids: Preparation and Applications

et al. 2019

View full text Add to dashboard Cite

Indole derivatives are associated with a variety of both biological activities and applications in the field of material chemistry. A number of different strategies for synthesizing substituted indoles by means of the reactions of indolylboronic acids with electrophilic compounds are considered the methods of choice for modifying indoles because indolylboronic acids are easily available, stable, non-toxic and new reactions using indolylboronic acids have been described in the literature. Thus, the aim of this review is to summarize the methods available for the preparation of indolylboronic acids as well as their chemical transformations. The review covers the period 2010–2019.

show abstract

Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(i)/Pd(0)/Cu(ii) cascade catalysis of 2-iodoaniline/phenols

Cited by 26 publications

References 51 publications

Towards the generalized iterative synthesis of small molecules

Towards the generalized iterative synthesis of small molecules

Scope and limitations of a DMF bio-alternative within Sonogashira cross-coupling and Cacchi-type annulation

Indolylboronic Acids: Preparation and Applications

Contact Info

Product

Resources

About