Snieckus Innovations

Kingston, Canada

Snieckus Innovations

Kingston, Canada
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Groom K.,Queen's University | Hussain S.M.S.,Queen's University | Hussain S.M.S.,King Fahd University of Petroleum and Minerals | Morin J.,Queen's University | And 4 more authors.
Organic Letters | Year: 2014

The regioselective synthesis of 2,3-di- and 1,2,3-trisubstituted naphthalenes via Directed ortho Metalation (DoM) strategies of N,N-diethyl-O-naphthyl-2-carbamate (1) is presented. Sequential LiTMP metalation-electrophile quench and s-BuLi/TMEDA (or t-BuLi)-electrophile quench of naphthyl-2-carbamate 1 provides a general route to contiguously substituted naphthalenes (6) with full regioselectivity. Further derivatization via ipso-halodesilylation and Suzuki-Miyaura cross-coupling leads ultimately to substituted halonaphthalenes and benzonaphthopyranones (9). © 2014 American Chemical Society.


Board J.,Snieckus Innovations | Cosman J.L.,Queen's University | Rantanen T.,Snieckus Innovations | Singh S.P.,Snieckus Innovations | Snieckus V.,Snieckus Innovations
Platinum Metals Review | Year: 2013

This review constitutes a detailed but non-exhaustive examination of the directed ortho metallation (DoM)-cross-coupling fusion in its many f avours. Special attention is paid to the application of the concept of the linked reactions and the synthetic utility that it endows, particularly in the case of one-pot reactions that can greatly increase the ease and eff ciency of the process. Personal experience of particular issues that can arise from these reactions and examples of their solutions are given, as well as illustrations of the rapid access to complex molecules that the technique encourages. © 2013 Johnson Matthey.


Balloch L.,University of Strathclyde | Garden J.A.,University of Strathclyde | Kennedy A.R.,University of Strathclyde | Mulvey R.E.,University of Strathclyde | And 3 more authors.
Angewandte Chemie - International Edition | Year: 2012

Metal detector: A bowl-shaped nanomolecule (see picture; S yellow, C gray, Zn blue) containing an unprecedented 16-atom [ZnC3]4 "anti-crown" ring has been unearthed by isolating a dizincated 2-substituted thiophene intermediate that would normally be hidden in tandem functionalization methodology. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Fuentes M.A.,University of Strathclyde | Kennedy A.R.,University of Strathclyde | Mulvey R.E.,University of Strathclyde | Parkinson J.A.,University of Strathclyde | And 3 more authors.
Chemistry - A European Journal | Year: 2015

Organometallic bases are becoming increasingly complex, because mixing components can lead to bases superior to single-component bases. To better understand this superiority, it is useful to study metalated intermediate structures prior to quenching. This study is on 1-phenyl-1H-benzotriazole, which was previously deprotonated by an in situ ZnCl2• TMEDA/LiTMP (TMEDA=N,N,N′,N′-tetramethylethylenediamine; TMP=2,2,6,6-tetramethylpiperidide) mixture and then iodinated. Herein, reaction with LiTMP exposes the deficiency of the single-component base as the crystalline product obtained was [{4-R-1-(2-lithiophenyl)-1H-benzotriazole• 3THF}2], [R=2-C6H4(Ph)NLi], in which ring opening of benzotriazole and N2 extrusion had occurred. Supporting lithiation by adding iBu2Al(TMP) induces trans-metal trapping, in which C-Li bonds transform into C-Al bonds to stabilise the metalated intermediate. X-ray diffraction studies revealed homodimeric [(4-R′-1-phenyl-1H-benzotriazole)2], [R′=(iBu)2Al(μ-TMP)Li], and its heterodimeric isomer [(4-R′-1-phenyl-1H-benzotriazole){2-R′-1-phenyl-1H-benzotriazole}], whose structure and slow conformational dynamics were probed by solution NMR spectroscopy. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


PubMed | University of Strathclyde, Snieckus Innovations and Queen's University
Type: Journal Article | Journal: Chemistry (Weinheim an der Bergstrasse, Germany) | Year: 2015

Organometallic bases are becoming increasingly complex, because mixing components can lead to bases superior to single-component bases. To better understand this superiority, it is useful to study metalated intermediate structures prior to quenching. This study is on 1-phenyl-1H-benzotriazole, which was previously deprotonated by an in situ ZnCl2 TMEDA/LiTMP (TMEDA=N,N,N,N-tetramethylethylenediamine; TMP=2,2,6,6-tetramethylpiperidide) mixture and then iodinated. Herein, reaction with LiTMP exposes the deficiency of the single-component base as the crystalline product obtained was [{4-R-1-(2-lithiophenyl)-1H-benzotriazole3THF}2 ], [R=2-C6 H4 (Ph)NLi], in which ring opening of benzotriazole and N2 extrusion had occurred. Supporting lithiation by adding iBu2 Al(TMP) induces trans-metal trapping, in which C-Li bonds transform into C-Al bonds to stabilise the metalated intermediate. X-ray diffraction studies revealed homodimeric [(4-R-1-phenyl-1H-benzotriazole)2 ], [R=(iBu)2 Al(-TMP)Li], and its heterodimeric isomer [(4-R-1-phenyl-1H-benzotriazole){2-R-1-phenyl-1H-benzotriazole}], whose structure and slow conformational dynamics were probed by solution NMR spectroscopy.


PubMed | Snieckus Innovations
Type: Journal Article | Journal: Organic letters | Year: 2014

The regioselective synthesis of 2,3-di- and 1,2,3-trisubstituted naphthalenes via Directed ortho Metalation (DoM) strategies of N,N-diethyl-O-naphthyl-2-carbamate (1) is presented. Sequential LiTMP metalation-electrophile quench and s-BuLi/TMEDA (or t-BuLi)-electrophile quench of naphthyl-2-carbamate 1 provides a general route to contiguously substituted naphthalenes (6) with full regioselectivity. Further derivatization via ipso-halodesilylation and Suzuki-Miyaura cross-coupling leads ultimately to substituted halonaphthalenes and benzonaphthopyranones (9).

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