Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes

María Frutos; Manuel A. Ortuño; Agustí Lledos; Alma Viso; Roberto Fernández De La Pradilla; María C. De La Torre; Miguel A. Sierra; Heinz Gornitzka; Catherine Hemmert

doi:10.1021/acs.orglett.6b03808

Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes

María Frutos, Manuel A. Ortuño, Agustí Lledos, Alma Viso, Roberto Fernández De La Pradilla, María C. De La Torre, Miguel A. Sierra, Heinz Gornitzka, Catherine Hemmert

Chemistry (Twin Cities)

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

13 Scopus citations

Abstract

New and well-characterized Ag-bis(1,2,3-triazolylidene) complexes having enantiopure (S)-sulfoxides upon sequential treatment with alcohols and Au(I) form separable mixtures of regioisomeric C-unsubstituted Au-1,2,3-triazolylidene complexes. Mechanistic studies and DFT calculations support a desulfinylation process for in situ generated free triazolylidene salts.

Original language	English (US)
Pages (from-to)	822-825
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.6b03808
State	Published - Feb 17 2017

Bibliographical note

Funding Information:
Support for this work under grants (CTQ2013-46459-C2-01-P to M.A.S., CTQ2013-46459-C2-02-P to M.C.T., and CTQ2014-51912-RDC) from the MINECO (Spain) is gratefully acknowledged. M.F. thanks the MINECO for FPI fellowship. Ms. M. Velado (CSIC) is acknowledged for helping with the preparation of some starting materials.

Publisher Copyright:
© 2017 American Chemical Society.

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title = "Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes",

abstract = "New and well-characterized Ag-bis(1,2,3-triazolylidene) complexes having enantiopure (S)-sulfoxides upon sequential treatment with alcohols and Au(I) form separable mixtures of regioisomeric C-unsubstituted Au-1,2,3-triazolylidene complexes. Mechanistic studies and DFT calculations support a desulfinylation process for in situ generated free triazolylidene salts.",

author = "Mar{\'i}a Frutos and Ortu{\~n}o, {Manuel A.} and Agust{\'i} Lledos and Alma Viso and {Fern{\'a}ndez De La Pradilla}, Roberto and {De La Torre}, {Mar{\'i}a C.} and Sierra, {Miguel A.} and Heinz Gornitzka and Catherine Hemmert",

note = "Funding Information: Support for this work under grants (CTQ2013-46459-C2-01-P to M.A.S., CTQ2013-46459-C2-02-P to M.C.T., and CTQ2014-51912-RDC) from the MINECO (Spain) is gratefully acknowledged. M.F. thanks the MINECO for FPI fellowship. Ms. M. Velado (CSIC) is acknowledged for helping with the preparation of some starting materials. Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = feb,

day = "17",

doi = "10.1021/acs.orglett.6b03808",

language = "English (US)",

volume = "19",

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journal = "Organic Letters",

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publisher = "American Chemical Society",

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T1 - Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes

T2 - Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes

AU - Frutos, María

AU - Ortuño, Manuel A.

AU - Lledos, Agustí

AU - Viso, Alma

AU - Fernández De La Pradilla, Roberto

AU - De La Torre, María C.

AU - Sierra, Miguel A.

AU - Gornitzka, Heinz

AU - Hemmert, Catherine

N1 - Funding Information: Support for this work under grants (CTQ2013-46459-C2-01-P to M.A.S., CTQ2013-46459-C2-02-P to M.C.T., and CTQ2014-51912-RDC) from the MINECO (Spain) is gratefully acknowledged. M.F. thanks the MINECO for FPI fellowship. Ms. M. Velado (CSIC) is acknowledged for helping with the preparation of some starting materials. Publisher Copyright: © 2017 American Chemical Society.

PY - 2017/2/17

Y1 - 2017/2/17

N2 - New and well-characterized Ag-bis(1,2,3-triazolylidene) complexes having enantiopure (S)-sulfoxides upon sequential treatment with alcohols and Au(I) form separable mixtures of regioisomeric C-unsubstituted Au-1,2,3-triazolylidene complexes. Mechanistic studies and DFT calculations support a desulfinylation process for in situ generated free triazolylidene salts.

AB - New and well-characterized Ag-bis(1,2,3-triazolylidene) complexes having enantiopure (S)-sulfoxides upon sequential treatment with alcohols and Au(I) form separable mixtures of regioisomeric C-unsubstituted Au-1,2,3-triazolylidene complexes. Mechanistic studies and DFT calculations support a desulfinylation process for in situ generated free triazolylidene salts.

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ER -

Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes

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