Synthesis of Previously Inaccessible Borylated Heterocycle Motifs Using Novel Boron‐Containing Amphoteric Molecules

Trinchera, Piera; Corless, Victoria B.; Yudin, Andrei K.

doi:10.1002/ange.201504271

Cited by 18 publications

(2 citation statements)

References 53 publications

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“…Therefore, a major strategy to generate C-boron enolates has been to stabilize the boron by quaternization (Figure ). This has led to elegant work culminating in the successful preparation and isolation of a number of stable C-boron enolates whose carbonyl functionality can be chemically manipulated, making them versatile precursors for the synthesis of various borylated compounds …”

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confidence: 99%

Synthesis and Applications of Unquaternized C-Bound Boron Enolates

Low

Chiu

2018

J. Am. Chem. Soc.

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A general and facile method to prepare unquaternized C-bound boron enolates by a ligand-controlled O-to-C isomerization is reported. Using this protocol, C-bound pinacolboron enolates have been isolated in pure form for the first time, and have been fully characterized by NMR spectroscopy and X-ray crystallography. In contrast to the general perception, such C-boron enolates are stable without coordinative saturation at the boron. Moreover, C-boron enolates present reactivities that are distinct from the O-boron enolates, and their applications in C-O and C-C bond formations are demonstrated.

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confidence: 99%

Synthesis and Applications of Unquaternized C-Bound Boron Enolates

Low

Chiu

2018

J. Am. Chem. Soc.

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“…[102–106] Moreover, recent reports from many different research groups demonstrate that a wide range of otherwise challenging-to-access MIDA boronate building blocks can be prepared from MIDA boronate starting materials. [91,93,96,99–106,107] Leveraging the advances described below, there is also ample opportunity to automate the process of building block synthesis, which has the potential to substantially increase the efficiency with which new building blocks can be sustainably accessed on-demand.…”

Section: One Machine – Many Small Moleculesmentioning

confidence: 99%

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

2018

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The eighteenth and nineteenth centuries marked a sweeping transition from manual to automated manufacturing on the macroscopic scale. This enabled an unmatched period of human innovation that helped drive the Industrial Revolution. The impact on society was transformative, ultimately yielding substantial improvements in living conditions and lifespan in many parts of the world. During the same time period, the first manual syntheses of organic molecules was achieved. Now, two centuries later, we are poised for an analogous transition from highly customized crafting of specific molecular targets by hand to the increasingly general and automated assembly of many different types of molecules with the push of a button. Automation of customized small molecule synthesis pathways is already enabling safer, more reproducible, and readily scalable production of specific targets, and general machines now exist for the synthesis of a wide range of different peptides, oligonucleotides, and oligosaccharides. Creating general machines that are similarly capable of making many different types of small molecules on-demand, akin to that which has been achieved on the macroscopic scale with 3D printers, has proven to be substantially more challenging. Yet important progress is being made toward this potentially transformative objective with two complementary approaches: (1) automation of customized synthesis routes to different targets via machines that enable use of many different reactions and starting materials, and (2) automation of generalized platforms that make many different targets using common coupling chemistry and building blocks. Continued progress in these exciting directions has the potential to shift the bottleneck in molecular innovation from synthesis to imagination, and thereby help drive a new industrial revolution on the molecular scale.

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Boron Trichloride‐Mediated Synthesis of Indoles via the Aminoboration of Alkynes

Liu

Han

et al. 2018

Adv Synth Catal

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We describe an efficient catalyst-and metal-free aminoboration of alkynes to 3-borylated indoles using one of the least expensive boron sources, BCl 3 . The major dichloro(indolyl)borane products can be used for the in situ construction of useful 3-Bpin indoles. This simple and mild method provides a novel and efficient approach for the synthesis of various 3-borylated indoles with high regioselectivity and a wide substrate scope.

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Synthesis of Previously Inaccessible Borylated Heterocycle Motifs Using Novel Boron‐Containing Amphoteric Molecules

Cited by 18 publications

References 53 publications

Synthesis and Applications of Unquaternized C-Bound Boron Enolates

Synthesis and Applications of Unquaternized C-Bound Boron Enolates

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

Boron Trichloride‐Mediated Synthesis of Indoles via the Aminoboration of Alkynes

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