Abstract
Carbon–hydrogen (C–H) bonds are ubiquitous in organic molecules, and methods for their selective functionalization to more reactive functional groups is a long-standing goal in catalysis, as applied to organic synthesis. Of the established methods involving transition metal catalysts, many employ carefully engineered substrate-catalyst interactions, placing the targeted C–H bond proximal to the metal catalyst, resulting in activation and subsequent functionalization. Here, we report mechanistic investigations describing a conceptual alternative to this approach whereby a cobalt-based borylation catalyst differentiates between subtle electronic differences in C(sp2)-H bonds of benzoate esters and arylboronate esters. These advances motivate studies of catalysts that rely on inherent differences in C–H bond electronics to distinguish chemically inequivalent sites, providing a new tool for organic synthesis.
Original language | English (US) |
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Pages (from-to) | 237-254 |
Number of pages | 18 |
Journal | Chem |
Volume | 7 |
Issue number | 1 |
DOIs | |
State | Published - Jan 14 2021 |
All Science Journal Classification (ASJC) codes
- General Chemistry
- General Chemical Engineering
- Biochemistry, medical
- Materials Chemistry
- Biochemistry
- Environmental Chemistry
Keywords
- C-H functionalization
- SDG12: Responsible consumption and production
- SDG3: Good health and well-being
- boron
- cobalt
- site selective