How Long to Read Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis

How Long Does it Take to Read Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis?

It takes the average reader 8 hours and 43 minutes to read Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis by Jonathan E. Dannatt

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Description

The studies in this dissertation are aimed at uncovering reactive and selective Ir-catalyzed C-H borylation (CHB) catalysts. Due to the high versatility of organoboron species, green methodology to produce the C-B bond is poised to support a myriad of subsequent transformations. These transformations include Suzuki couplings, aminations, oxidations, halogenations, cyanations, and trifluoromethylations.Typical iridium catalyzed CHBs proceed through an iridium trisboryl with a bidentate ligand such as bipyridine or 1,10-phenanthroline. The selectivity of these standard catalysts is generally driven by sterics; however, many methods of overcoming the steric bias have been developed in the two decades since the first thermal catalytic C-H activation borylation. These methods include both inner- and outer-sphere directed mechanisms. Outer-sphere directed borylations have been accomplished by leveraging hydrogen bonding, Lewis acid-base, and ion-pairing as directing elements. In general this reactivity is activated by precise design of the bidentate ligand framework.Herein is reported a subtle electrostatic interaction to direct ortho-borylation of phenols by simply switching boron source from the common B2pin2 (pin = pinacolate) to B2eg2 (eg = ethyleneglycolate). This electrostatic interaction was revealed by a careful computational analysis of key C-H activation transition states. Understanding gained by the computational studies led to the redesign of the boron source which enabled by selectivities of > 99% ortho borylation. This methodology was extended to the highly selective ortho-borylation of anilines, and the underlying mechanism has been interrogated.Currently, iridium based catalysts have been generated to borylate ortho, meta, and even para to a variety of classes of substrates; however, control of selectivity can breakdown in many fluorinated arenes without a directing group. These substrates are challenging because the fluoro moiety being similar in size to a hydrogen offers little in the way of steric bias. While working to overcome these challenges, a serendipitously discovered hydrazone based ligand was discovered. Exploration of the catalysts generated by this ligand revealed not only impressive activity rivaling dtbpy but also incredible selectivity for meta to a fluoro group.In general iridium CHB catalysts selectively activate sp2 C-H bonds leaving all sp3 C-H bonds intact; however, a method to turn on sp3 C-H activation would be desirable. It was reasoned that a directing group able to increase the effective concentration of the iridium catalyst near a C(sp3)-H bond may enable this transformation. Indeed, it was discovered that catalysts able to accept amide directing groups were able to selectively borylate compounds with amide N-methyl substituents.

How long is Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis?

Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis by Jonathan E. Dannatt is 521 pages long, and a total of 130,771 words.

This makes it 176% the length of the average book. It also has 160% more words than the average book.

How Long Does it Take to Read Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis Aloud?

The average oral reading speed is 183 words per minute. This means it takes 11 hours and 54 minutes to read Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis aloud.

What Reading Level is Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis?

Advancing Frontiers in Reactive and Selective Iridium C-h Borylation Catalysis and Targeted Silsesquioxane Synthesis is suitable for students ages 12 and up.

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