Scope and Limitations of the PdCl <sub>2</sub> (MeCN) <sub>2</sub> /Fe(OTf) <sub>3</sub> -Cocatalyzed Aerobic Olefin Aminoboration
Herein, we report the Pd(II)/Fe(III)-cocatalyzed aerobic aminoboration of norbornene with nitrogen nucleophiles and B<sub>2</sub>pin<sub>2</sub>, employing 10 mol % Fe(OTf)<sub>3</sub> cocatalyst. These conditions are limited to strained cyclic olefins; α-olefins fail to produce appreciable yields under the reaction conditions. The reaction scope is demonstrated for the aminoboration of norbornene with an array of nitrogen nucleophiles (27 examples with up to 98% isolated yield), including imides, sulfonamides, and amides. Moreover, mechanistic investigations demonstrate that Fe(OTf)<sub>3</sub> promotes rapid transmetalation with B<sub>2</sub>pin<sub>2</sub>; with activated strained cyclic alkenes, this increases the rate of aminoboration. Conversely, with less active α-olefins, the oxidative degradation of B<sub>2</sub>pin<sub>2</sub> is faster than aminoboration.
Authors
- Shreeja Bhatt (ORCID: https://orcid.org/0000-0003-3262-2894)
- Kami L. Hull (ORCID: https://orcid.org/0000-0003-3102-2686)
- Brittany L. Gay (ORCID: https://orcid.org/0000-0002-6481-6071)
- Lillian M. Skinner
- E. Grace Milem
- Ya-Nong Wang
Institutions
- The University of Texas at Austin (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2026-02-24
- DOI
- https://doi.org/10.1021/acs.joc.5c02911
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00