Boronyl Borinic Esters: Preparation as B2pin2/secBuLi/TFAA Adducts, Structural Insights and Reactivity in Pd‐catalyzed Allylic Borylation

Boronyl Borinic Esters: Preparation as B2pin2/secBuLi/TFAA Adducts, Structural Insights and Reactivity in Pd‐catalyzed Allylic Borylation Full article

Journal

Chemistry-An Asian Journal
ISSN: 1861-471X , E-ISSN: 1861-4728

Output data

Year: 2023, Volume: 18, Number: 12, Article number : e202300219, Pages count : DOI: 10.1002/asia.202300219

Authors

Novikov Maxim A ¹ , Novikov Roman A ¹ , Tomilov Yury V ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation

Novel boronyl borinic ester I was generated by quenching the B2pin2/secBuLi-ate complex with trifluoroacetic acid anhydride (TFAA) via ring-opening in the 1,3,2-dioxaborolane moiety on ate-boron. Detailed NMR studies of the B2pin2/secBuLi-ate complex in solution and in solid state allowed us to assume its oligomeric nature in solids with only ate-boron involved in the oligomerization process. The O-trifluoroacetyl pinacolate residue on borinic ester I initially formed on quenching with TFAA undergoes an unusual intramolecular transesterification with the carbonyl group of trifluoroacetyl forming othroester moiety in a few hours at r. t. to give boronyl borinic ester II. A solution of these reagents I/II was proved to be efficient for borylation of (2-fluoroallyl)pyridinium salts that are highly base sensitive.

Novikov M.A. , Novikov R.A. , Tomilov Y.V.
Boronyl Borinic Esters: Preparation as B2pin2/secBuLi/TFAA Adducts, Structural Insights and Reactivity in Pd‐catalyzed Allylic Borylation
Chemistry-An Asian Journal. 2023. V.18. N12. e202300219 . DOI: 10.1002/asia.202300219 WOS Scopus OpenAlex

≡ Web of science:	WOS:000989598200001
≡ Scopus:	2-s2.0-85159424112
≡ OpenAlex:	W4367299423