TY - JOUR
T1 - One-Pot Synthesis of Unprotected 2-Acylpyrroles from 1,2,3-Triazoles and 2-Hydroxymethylallyl Carbonates
AU - Park, Jong Un
AU - Huang, Liang Zhu
AU - Cho, Ho Jun
AU - Park, Boyoung Y.
AU - Kim, Ju Hyun
N1 - Publisher Copyright:
© 2022 American Chemical Society.
PY - 2023/1/6
Y1 - 2023/1/6
N2 - An efficient, tandem one-pot approach to synthesize multisubstituted 2-acylpyrroles from readily prepared N-tosyl triazoles and 2-hydroxymethylallyl carbonates is reported. The reaction proceeds via Rh(II)-catalyzed O-H insertion, [3,3]-sigmatropic rearrangement, Pd(0)-catalyzed oxidative addition, intramolecular cyclization, DBU-promoted E1cB elimination, double bond isomerization, and aromatization, enabling the disconnection and formation of multiple bonds in one reactor. The approach represents a highly regioselective way to access di-, tri-, and tetra-substituted NH pyrroles with high efficiency.
AB - An efficient, tandem one-pot approach to synthesize multisubstituted 2-acylpyrroles from readily prepared N-tosyl triazoles and 2-hydroxymethylallyl carbonates is reported. The reaction proceeds via Rh(II)-catalyzed O-H insertion, [3,3]-sigmatropic rearrangement, Pd(0)-catalyzed oxidative addition, intramolecular cyclization, DBU-promoted E1cB elimination, double bond isomerization, and aromatization, enabling the disconnection and formation of multiple bonds in one reactor. The approach represents a highly regioselective way to access di-, tri-, and tetra-substituted NH pyrroles with high efficiency.
UR - http://www.scopus.com/inward/record.url?scp=85144443770&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.2c02602
DO - 10.1021/acs.joc.2c02602
M3 - Article
AN - SCOPUS:85144443770
SN - 0022-3263
VL - 88
SP - 585
EP - 593
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 1
ER -