Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

J.M. Aizpurua; M. Sagartzazu-Aizpurua; Z. Monasterio; I. Azcune; C. Mendicute; J.I. Miranda; E. Garcia-Lecina; A. Altube; R.M. Fratila

doi:10.1021/ol3004657

Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

J.M. Aizpurua, M. Sagartzazu-Aizpurua, Z. Monasterio, I. Azcune, C. Mendicute, J.I. Miranda, E. Garcia-Lecina, A. Altube, R.M. Fratila

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Abstract

Mesoionic 4,4′-bis(1,2,3-triazole-5,5′-diylidene) Rh(I) complexes having a C2 chiral 4,4′-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.

Original language	English
Pages (from-to)	1866-1868
Journal	Organic letters
Volume	14
Issue number	7
DOIs	https://doi.org/10.1021/ol3004657
Publication status	Published - 2012

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title = "Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes",

abstract = "Mesoionic 4,4′-bis(1,2,3-triazole-5,5′-diylidene) Rh(I) complexes having a C2 chiral 4,4′-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.",

author = "J.M. Aizpurua and M. Sagartzazu-Aizpurua and Z. Monasterio and I. Azcune and C. Mendicute and J.I. Miranda and E. Garcia-Lecina and A. Altube and R.M. Fratila",

year = "2012",

doi = "10.1021/ol3004657",

language = "English",

volume = "14",

pages = "1866--1868",

journal = "Organic letters",

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publisher = "American Chemical Society",

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T1 - Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

AU - Aizpurua, J.M.

AU - Sagartzazu-Aizpurua, M.

AU - Monasterio, Z.

AU - Azcune, I.

AU - Mendicute, C.

AU - Miranda, J.I.

AU - Garcia-Lecina, E.

AU - Altube, A.

AU - Fratila, R.M.

PY - 2012

Y1 - 2012

N2 - Mesoionic 4,4′-bis(1,2,3-triazole-5,5′-diylidene) Rh(I) complexes having a C2 chiral 4,4′-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.

AB - Mesoionic 4,4′-bis(1,2,3-triazole-5,5′-diylidene) Rh(I) complexes having a C2 chiral 4,4′-axis were accessed from 3-alkyltriazolium salts in virtually complete de. Their structure and configurational integrity were assessed by NMR spectroscopy, X-ray crystallography, and chiral HPLC. Computational analysis of the MICs involved in the reaction suggested the formation of a highly stable and unprecedented cation-carbene intermediate species, which could be evidenced experimentally by cyclic voltammetry analysis.

U2 - 10.1021/ol3004657

DO - 10.1021/ol3004657

M3 - Article

SN - 1523-7060

VL - 14

SP - 1866

EP - 1868

JO - Organic letters

JF - Organic letters

IS - 7

ER -

Introducing Axial Chirality into Mesoionic 4,4′-Bis(1,2,3-triazole) Dicarbenes

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