Balancing Reactivity, Regioselectivity, and Product Stability in Ir-Catalyzed Ortho-C-H Borylations of Anilines by Modulating the Diboron Partner.

Autor: Montero Bastidas JR; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States., Yadav A; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States., Lee S; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States., Ghaffari B; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States., Smith MR 3rd; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States., Maleczka RE Jr; Department of Chemistry, Michigan State University, 578 South Shaw Lane, East Lansing, Michigan 48824, United States.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Jul 05; Vol. 26 (26), pp. 5420-5424. Date of Electronic Publication: 2024 Jun 26.
DOI: 10.1021/acs.orglett.4c01495
Abstrakt: Ir-catalyzed arene C-H borylations (CHB) of anilines can be highly ortho selective by using a small B 2 eg 2 (eg = ethane-1,2-diol) as the borylating reagent. Unfortunately, the products are prone to decomposition, and transesterification with pinacol is required prior to isolation. This work offers a solution by adjusting the size of the diboron reagent. Based on our evaluation, we conclude that B 2 bg 2 (bg = butane-1,2-diol) achieves an optimal balance between CHB regioselectivity and stability for the borylated products.
Databáze: MEDLINE