Synthesis of novel tantalacalixarene complexes: First example of intramolecular CH activation of monodepleted aromatic ring

Jeff Espinas; Jérémie Pelletier; Erwan Jeanneau; Ulrich Darbost; Kai C. Szeto; Christine Lucas; Jean Thivolle-Cazat; Christian Duchamp; Natali Henriques; Denis Bouchu; Jean Marie Basset; Henry Chermette; Isabelle Bonnamour; Mostafa Taoufik

doi:10.1021/om200140u

Synthesis of novel tantalacalixarene complexes: First example of intramolecular CH activation of monodepleted aromatic ring

Jeff Espinas, Jérémie Pelletier, Erwan Jeanneau, Ulrich Darbost, Kai C. Szeto, Christine Lucas, Jean Thivolle-Cazat, Christian Duchamp, Natali Henriques, Denis Bouchu, Jean Marie Basset, Henry Chermette^*, Isabelle Bonnamour, Mostafa Taoufik

^*Corresponding author for this work

Physical Sciences and Engineering

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

The alkylation of (dichlorotantala)-p-tert-butylcalix[4]arenes 1 and 3 by two equivalents of NpMgCl (Np = neopentyl) affords the corresponding unreported (bisneopentyltantala)-p-tert-butylcalix[4]arenes 4 and 5. These complexes can undergo dealkylation by modest increase of the temperature to yield 6 and 7. The characterization and structural conformation of the complexes 6 and 7 were determined by ¹H, ¹³C, NOESY, and COSY spectroscopic studies and single-crystal X-ray diffraction. 7 exhibits unprecedented use of an intramolecular C-H activation of an aromatic ring and simultaneously releases of one equivalent of neopentane. DFT calculation supports a mechanism in which the metal passes through a transition state involving a coplanar arrangement with its three ligands (C_Ar, H_Ar, C_Np).

Original language	English (US)
Pages (from-to)	3512-3521
Number of pages	10
Journal	Organometallics
Volume	30
Issue number	13
DOIs	https://doi.org/10.1021/om200140u
State	Published - Jul 11 2011

ASJC Scopus subject areas

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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Espinas, J., Pelletier, J., Jeanneau, E., Darbost, U., Szeto, K. C., Lucas, C., Thivolle-Cazat, J., Duchamp, C., Henriques, N., Bouchu, D., Basset, J. M., Chermette, H., Bonnamour, I., & Taoufik, M. (2011). Synthesis of novel tantalacalixarene complexes: First example of intramolecular CH activation of monodepleted aromatic ring. Organometallics, 30(13), 3512-3521. https://doi.org/10.1021/om200140u

@article{29898398c86c42a0ba9a99d1b6e265ad,

title = "Synthesis of novel tantalacalixarene complexes: First example of intramolecular CH activation of monodepleted aromatic ring",

abstract = "The alkylation of (dichlorotantala)-p-tert-butylcalix[4]arenes 1 and 3 by two equivalents of NpMgCl (Np = neopentyl) affords the corresponding unreported (bisneopentyltantala)-p-tert-butylcalix[4]arenes 4 and 5. These complexes can undergo dealkylation by modest increase of the temperature to yield 6 and 7. The characterization and structural conformation of the complexes 6 and 7 were determined by 1H, 13C, NOESY, and COSY spectroscopic studies and single-crystal X-ray diffraction. 7 exhibits unprecedented use of an intramolecular C-H activation of an aromatic ring and simultaneously releases of one equivalent of neopentane. DFT calculation supports a mechanism in which the metal passes through a transition state involving a coplanar arrangement with its three ligands (CAr, HAr, CNp).",

author = "Jeff Espinas and J{\'e}r{\'e}mie Pelletier and Erwan Jeanneau and Ulrich Darbost and Szeto, {Kai C.} and Christine Lucas and Jean Thivolle-Cazat and Christian Duchamp and Natali Henriques and Denis Bouchu and Basset, {Jean Marie} and Henry Chermette and Isabelle Bonnamour and Mostafa Taoufik",

year = "2011",

month = jul,

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doi = "10.1021/om200140u",

language = "English (US)",

volume = "30",

pages = "3512--3521",

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Espinas, J, Pelletier, J, Jeanneau, E, Darbost, U, Szeto, KC, Lucas, C, Thivolle-Cazat, J, Duchamp, C, Henriques, N, Bouchu, D, Basset, JM, Chermette, H, Bonnamour, I & Taoufik, M 2011, 'Synthesis of novel tantalacalixarene complexes: First example of intramolecular CH activation of monodepleted aromatic ring', Organometallics, vol. 30, no. 13, pp. 3512-3521. https://doi.org/10.1021/om200140u

TY - JOUR

T1 - Synthesis of novel tantalacalixarene complexes

T2 - First example of intramolecular CH activation of monodepleted aromatic ring

AU - Espinas, Jeff

AU - Pelletier, Jérémie

AU - Jeanneau, Erwan

AU - Darbost, Ulrich

AU - Szeto, Kai C.

AU - Lucas, Christine

AU - Thivolle-Cazat, Jean

AU - Duchamp, Christian

AU - Henriques, Natali

AU - Bouchu, Denis

AU - Basset, Jean Marie

AU - Chermette, Henry

AU - Bonnamour, Isabelle

AU - Taoufik, Mostafa

PY - 2011/7/11

Y1 - 2011/7/11

N2 - The alkylation of (dichlorotantala)-p-tert-butylcalix[4]arenes 1 and 3 by two equivalents of NpMgCl (Np = neopentyl) affords the corresponding unreported (bisneopentyltantala)-p-tert-butylcalix[4]arenes 4 and 5. These complexes can undergo dealkylation by modest increase of the temperature to yield 6 and 7. The characterization and structural conformation of the complexes 6 and 7 were determined by 1H, 13C, NOESY, and COSY spectroscopic studies and single-crystal X-ray diffraction. 7 exhibits unprecedented use of an intramolecular C-H activation of an aromatic ring and simultaneously releases of one equivalent of neopentane. DFT calculation supports a mechanism in which the metal passes through a transition state involving a coplanar arrangement with its three ligands (CAr, HAr, CNp).

AB - The alkylation of (dichlorotantala)-p-tert-butylcalix[4]arenes 1 and 3 by two equivalents of NpMgCl (Np = neopentyl) affords the corresponding unreported (bisneopentyltantala)-p-tert-butylcalix[4]arenes 4 and 5. These complexes can undergo dealkylation by modest increase of the temperature to yield 6 and 7. The characterization and structural conformation of the complexes 6 and 7 were determined by 1H, 13C, NOESY, and COSY spectroscopic studies and single-crystal X-ray diffraction. 7 exhibits unprecedented use of an intramolecular C-H activation of an aromatic ring and simultaneously releases of one equivalent of neopentane. DFT calculation supports a mechanism in which the metal passes through a transition state involving a coplanar arrangement with its three ligands (CAr, HAr, CNp).

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DO - 10.1021/om200140u

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SN - 0276-7333

VL - 30

SP - 3512

EP - 3521

JO - Organometallics

JF - Organometallics

IS - 13

ER -

Synthesis of novel tantalacalixarene complexes: First example of intramolecular CH activation of monodepleted aromatic ring

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