Synthesis Workshop: Meta-selective C-H Borylation with Dr. Tyler Pabst (Episode 106)

In this Research Spotlight episode, Dr. Tyler Pabst (alumnus of Chirik group at Princeton) joins us to share his work on meta-selective C-H borylation reactions enabled by cobalt catalysis.

Key references:
Organometallics 2021, 40, 813-831.
https://doi.org/10.1021/acs.organomet...
J. Am. Chem. Soc. 2019, 141, 15378-15389.
https://doi.org/10.1021/jacs.9b07984
Chem 2021, 7, 237-254.
https://doi.org/10.1016/j.chempr.2020...
J. Am. Chem. Soc. 2022, 144, 6465-6474.
https://doi.org/10.1021/jacs.2c01162

Additional references (in order of appearance):
See also: J. Am. Chem. Soc. 2020, 142, 10571-10591.
Chem. Rev. 2010, 110, 890-931.
Seminal Reports: J. Am. Chem. Soc. 2002, 124, 390-391; Science 2002, 295, 305-306.
J. Am. Chem. Soc. 2017, 139, 2825-2832.
Fluorine in pharmaceuticals: J. Fluor. Chem. 2013, 152, 119-128; J. Med. Chem. 2018, 61, 5822-5880.
Rare ex. of selective Ir-cat. fluoroarene borylation: Org. Lett. 2019, 21, 6388−6392; ACS Catal. 2021, 11, 5968−5973.
Computational study on (PNP)Co-catalyzed benzene borylation: ACS Catal. 2018, 8, 10606-10618.
Organometallics 1994, 13, 522-532.
Computational study on the ortho fluorine effect: J. Am. Chem. Soc. 2009, 131, 7817-7827.
Computational study on (PNP)Co-catalyzed benzene borylation: ACS Catal. 2018, 8, 10606-10618.
First observation of para-to-boronate regioselectivity in C–H borylation: J. Am. Chem. Soc. 2005, 127, 10539-10544.
Ir-catalyzed meta-to-FG selective borylation: Science 2022, 375, 658-663.
First report of (terpyridine)Co-catalyzed C–H borylation: Organometallics 2017, 36, 142-150.
Synthesis and isolation of (PNP)Co boryl: J. Am. Chem. Soc. 2016, 138, 10645-10653.
On the interpretation of deuterium KIEs: Angew. Chem. Int. Ed. 2012, 51, 3066-3072.
More on RMC/CH for fluoroarenes: Acc. Chem. Res. 2011, 44, 333-348; Organometallics 2021, 40, 813-831.