PMID- 29251365
OWN - NLM
STAT- PubMed-not-MEDLINE
DCOM- 20180321
LR  - 20180321
IS  - 1521-3765 (Electronic)
IS  - 0947-6539 (Linking)
VI  - 24
IP  - 11
DP  - 2018 Feb 21
TI  - Investigations of the Copper-Catalyzed Oxidative Cross-Coupling of 
      Tetrahydroisoquinolines with Diethylzinc by a Combination of Mass Spectrometric 
      and Electrochemical Methods.
PG  - 2663-2668
LID - 10.1002/chem.201704914 [doi]
AB  - The aerobic oxidative cross-coupling of tetrahydroisoquinolines (THIQs) with 
      diethylzinc catalyzed by CuCl(2) has been examined by means of electrospray mass 
      spectrometry (ESI-MS). Substrates, intermediates, and the product were readily 
      detected. Particular emphasis has been placed on the role of CuCl(2) . Formation 
      of the intermediate iminium species has been investigated in more detail by 
      ESI-MS, electrochemistry-coupled ESI mass spectrometry (EC-MS), and cyclic 
      voltammetry (CV). Our experiments have consistently revealed strong influences of 
      the N-substituent of the THIQ derivative and its oxidation stability with respect 
      to CuCl(2) . The results may help to expand the synthetic scope of the reaction, 
      while also further establishing EC-MS as a valuable technique for linking mass 
      spectrometry with cyclic voltammetry in mechanistic studies of organic redox 
      reactions.
CI  - (c) 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
FAU - Willms, J Alexander
AU  - Willms JA
AD  - Kekule-Institute of Organic Chemistry and Biochemistry, University of Bonn, 
      Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
FAU - Gleich, Hermann
AU  - Gleich H
AD  - Kekule-Institute of Organic Chemistry and Biochemistry, University of Bonn, 
      Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
FAU - Schrempp, Michael
AU  - Schrempp M
AD  - Kekule-Institute of Organic Chemistry and Biochemistry, University of Bonn, 
      Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
FAU - Menche, Dirk
AU  - Menche D
AD  - Kekule-Institute of Organic Chemistry and Biochemistry, University of Bonn, 
      Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
FAU - Engeser, Marianne
AU  - Engeser M
AUID- ORCID: 0000-0001-6987-4126
AD  - Kekule-Institute of Organic Chemistry and Biochemistry, University of Bonn, 
      Gerhard-Domagk-Strasse 1, 53121, Bonn, Germany.
LA  - eng
PT  - Journal Article
DEP - 20180126
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
OTO - NOTNLM
OT  - Cu catalysis
OT  - cross-coupling
OT  - cyclic voltammetry
OT  - electrospray mass spectrometry
OT  - tetrahydroisoquinoline
EDAT- 2017/12/19 06:00
MHDA- 2017/12/19 06:01
CRDT- 2017/12/19 06:00
PHST- 2017/10/16 00:00 [received]
PHST- 2017/12/19 06:00 [pubmed]
PHST- 2017/12/19 06:01 [medline]
PHST- 2017/12/19 06:00 [entrez]
AID - 10.1002/chem.201704914 [doi]
PST - ppublish
SO  - Chemistry. 2018 Feb 21;24(11):2663-2668. doi: 10.1002/chem.201704914. Epub 2018 
      Jan 26.