TY - JOUR
T1 - 1,3-Aza-Brook Rearrangement of Aniline Derivatives
T2 - In Situ Generation of 3-Aminoaryne via 1,3-C-(sp2)-to-N Silyl Migration
AU - Jeon, Young Kyo
AU - Kim, Won Suk
N1 - Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) (NRF-2019M1A2A2072417, NRF-2021R1H1A2014525, NRF-2021R1A6A1A10039823).
Publisher Copyright:
© 2021 American Chemical Society.
PY - 2021/10/1
Y1 - 2021/10/1
N2 - The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp2)-to-N 1,3-aza-Brook rearrangement have been achieved, allowing access to diverse aniline derivatives. Through crossover experiments, we demonstrated the intramolecular mechanism of 1,3-C-to-N silyl transfer. To gain insight into the regioselectivity observed in the reactions, we performed density functional theory calculations. Finally, the method was applied to the synthesis of xylanigripones A in five linear steps in an overall yield of 30%.
AB - The design, synthesis, and validation of 3-aminobenzyne precursors induced by C-(sp2)-to-N 1,3-aza-Brook rearrangement have been achieved, allowing access to diverse aniline derivatives. Through crossover experiments, we demonstrated the intramolecular mechanism of 1,3-C-to-N silyl transfer. To gain insight into the regioselectivity observed in the reactions, we performed density functional theory calculations. Finally, the method was applied to the synthesis of xylanigripones A in five linear steps in an overall yield of 30%.
UR - http://www.scopus.com/inward/record.url?scp=85116579160&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.1c02751
DO - 10.1021/acs.orglett.1c02751
M3 - Article
C2 - 34553933
AN - SCOPUS:85116579160
VL - 23
SP - 7545
EP - 7549
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 19
ER -