Transient-Directing Group-Enabled Manganese-Catalyzed C–H Alkylation
- 1Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstraße 2, 37077 Göttingen, Germany
Abstract
The construction of C–C bonds by manganese-catalyzed C–H activation thus far relies on permanent directing groups that need to be installed and removed, while the use of transient directing groups remains an elusive challenge. In sharp contrast, we herein describe a manganese-catalyzed intramolecular C–H alkylation of indole-3-carboxaldehydes enabled by the use of a transient directing group in catalytic quantities. Our strategy provided access to a wide range of N1/C2-fused polycyclic indoles, generating a tertiary C-center in excellent yields and concomitant good functional group tolerance. The desired polycyclic indole underwent late-stage diversification guided by the native formyl directing group through C4–H activation, as well as leading to the decoration with barbituric acid moiety. Additionally, computational mechanistic insight by DFT provided support for a rate-determining migratory insertion.
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BibTeX
@article{connon2026transientdirecting,
title = {{Transient-Directing Group-Enabled Manganese-Catalyzed C–H Alkylation}},
author = {Robert Connon and Isaac Maksso and Matthias M. Simon and Zi-Jing Zhang and Binbin Yuan and Lutz Ackermann},
journal = {Organic Letters},
year = {2026},
month = oct,
doi = {10.1021/acs.orglett.6c03470},
url = {https://doi.org/10.1021/acs.orglett.6c03470},
note = {CC BY 4.0},
}
RIS
TY - JOUR
TI - Transient-Directing Group-Enabled Manganese-Catalyzed C–H Alkylation
AU - Robert Connon
AU - Isaac Maksso
AU - Matthias M. Simon
AU - Zi-Jing Zhang
AU - Binbin Yuan
AU - Lutz Ackermann
PY - 2026
DA - 2026/10/09
JO - Organic Letters
DO - 10.1021/acs.orglett.6c03470
UR - https://doi.org/10.1021/acs.orglett.6c03470
AB - The construction of C–C bonds by manganese-catalyzed C–H activation thus far relies on permanent directing groups that need to be installed and removed, while the use of transient directing groups remains an elusive challenge. In sharp contrast, we herein describe a manganese-catalyzed intramolecular C–H alkylation of indole-3-carboxaldehydes enabled by the use of a transient directing group in catalytic quantities. Our strategy provided access to a wide range of N1/C2-fused polycyclic indoles, generating a tertiary C-center in excellent yields and concomitant good functional group tolerance. The desired polycyclic indole underwent late-stage diversification guided by the native formyl directing group through C4–H activation, as well as leading to the decoration with barbituric acid moiety. Additionally, computational mechanistic insight by DFT provided support for a rate-determining migratory insertion.
SN - 1523-7060
SN - 1523-7052
ER -