Tags

Type your tag names separated by a space and hit enter

An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp*MCl2]2 (M = Rh, Ir).
J Am Chem Soc. 2008 Sep 17; 130(37):12414-9.JA

Abstract

Bi-, tri-, and tetracyclic isoquinoline salts were readily synthesized in excellent yields at room temperature from readily available starting materials after three reaction steps. Aromatic C-H activation was first promoted by sodium acetate with [Cp*MCl2]2 (M = Rh, Ir) at room temperature to form cyclometalated compounds. Dimethylacetylenedicarboxylate was then found to insert into the metal-carbon bonds of the cyclometalated compounds. Finally, the insertion compounds underwent oxidative coupling to form the desired isoquinoline salts and regenerate [Cp*MCl2]2. All of the intermediate compounds following C-H activation, alkyne insertion, and oxidative coupling were fully characterized, including the determination of X-ray structures in several cases, and the results shed light on the overall mechanism. Moreover, it was possible to synthesize the isoquinoline salts from readily available starting materials using one-pot procedures; thus, this work provides a novel, efficient method for metal-mediated synthesis of heterocycles.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Li L
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
Brennessel WW
No affiliation info available
Jones WD
No affiliation info available

MeSH

Cold TemperatureCrystallography, X-RayIridiumIsoquinolinesMagnetic Resonance SpectroscopyOrganometallic CompoundsRhodium

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, Non-P.H.S.

Language

eng

PubMed ID

18714995

Citation

Li, Ling, et al. "An Efficient Low-temperature Route to Polycyclic Isoquinoline Salt Synthesis Via C-H Activation With [Cp*MCl2]2 (M = Rh, Ir)." Journal of the American Chemical Society, vol. 130, no. 37, 2008, pp. 12414-9.
Li L, Brennessel WW, Jones WD. An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp*MCl2]2 (M = Rh, Ir). J Am Chem Soc. 2008;130(37):12414-9.
Li, L., Brennessel, W. W., & Jones, W. D. (2008). An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp*MCl2]2 (M = Rh, Ir). Journal of the American Chemical Society, 130(37), 12414-9. https://doi.org/10.1021/ja802415h
Li L, Brennessel WW, Jones WD. An Efficient Low-temperature Route to Polycyclic Isoquinoline Salt Synthesis Via C-H Activation With [Cp*MCl2]2 (M = Rh, Ir). J Am Chem Soc. 2008 Sep 17;130(37):12414-9. PubMed PMID: 18714995.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp*MCl2]2 (M = Rh, Ir). AU - Li,Ling, AU - Brennessel,William W, AU - Jones,William D, Y1 - 2008/08/21/ PY - 2008/8/22/pubmed PY - 2008/10/29/medline PY - 2008/8/22/entrez SP - 12414 EP - 9 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 130 IS - 37 N2 - Bi-, tri-, and tetracyclic isoquinoline salts were readily synthesized in excellent yields at room temperature from readily available starting materials after three reaction steps. Aromatic C-H activation was first promoted by sodium acetate with [Cp*MCl2]2 (M = Rh, Ir) at room temperature to form cyclometalated compounds. Dimethylacetylenedicarboxylate was then found to insert into the metal-carbon bonds of the cyclometalated compounds. Finally, the insertion compounds underwent oxidative coupling to form the desired isoquinoline salts and regenerate [Cp*MCl2]2. All of the intermediate compounds following C-H activation, alkyne insertion, and oxidative coupling were fully characterized, including the determination of X-ray structures in several cases, and the results shed light on the overall mechanism. Moreover, it was possible to synthesize the isoquinoline salts from readily available starting materials using one-pot procedures; thus, this work provides a novel, efficient method for metal-mediated synthesis of heterocycles. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/18714995/An_efficient_low_temperature_route_to_polycyclic_isoquinoline_salt_synthesis_via_C_H_activation_with_[Cp_MCl2]2__M_=_Rh_Ir__ L2 - https://doi.org/10.1021/ja802415h DB - PRIME DP - Unbound Medicine ER -