PMID- 32351111
OWN - NLM
STAT- PubMed-not-MEDLINE
LR  - 20201120
IS  - 1520-6904 (Electronic)
IS  - 0022-3263 (Linking)
VI  - 85
IP  - 22
DP  - 2020 Nov 20
TI  - Toward N,P-Doped pi-Extended PAHs: A One-Pot Synthesis to Diannulated 
      1,4,2-Diazaphospholium Triflate Salts.
PG  - 14420-14434
LID - 10.1021/acs.joc.0c00577 [doi]
AB  - A novel method for the one-pot synthesis of diannulated 1,4,2-diazaphospholium 
      triflate salts by a Me(3)SiOTf-mediated self-condensation of dichlorophosphaneyl 
      aza-(poly)cyclic aromatic hydrocarbons (aza-(P)AHs; namely, pyridine, quinoline, 
      phenanthridine, and benzo[d]thiazole) is reported. The diannulated 
      1,4,2-diazaphospholium triflate salts are characterized by multinuclear NMR 
      spectroscopy, X-ray analysis, as well as their calculated NICS values, 
      underlining their aromatic character. Quantum mechanical calculations shed light 
      on the intermolecular reaction mechanism. Follow up chemistry, such as the 
      halogenation reaction with XeF(2) or SO(2)Cl(2) with the dipyridinium derivative 
      selectively yields the respective dihalo-sigma(4),lambda(5)- and 
      tetrahalo-sigma(5),lambda(6)-diazaphospholium triflate salts. The 
      dihalo-sigma(4),lambda(5)-diazaphospholium triflate salt serves well as a surrogate for 
      the introduction of the cationic 2-(1,2'-bipyridin)-1-iumyl ligand (1,2'-bipyl), 
      the monocationic structural isomer of the prototypical 2,2'-bipyridine ligand 
      (2,2'-bipy).
FAU - Schoemaker, Robin
AU  - Schoemaker R
AD  - Faculty of Chemistry and Food Chemistry, Technische Universitat Dresden, Dresden 
      01062, Germany.
FAU - Schwedtmann, Kai
AU  - Schwedtmann K
AD  - Faculty of Chemistry and Food Chemistry, Technische Universitat Dresden, Dresden 
      01062, Germany.
FAU - Hennersdorf, Felix
AU  - Hennersdorf F
AUID- ORCID: 0000-0002-3729-030X
AD  - Faculty of Chemistry and Food Chemistry, Technische Universitat Dresden, Dresden 
      01062, Germany.
FAU - Bauza, Antonio
AU  - Bauza A
AUID- ORCID: 0000-0002-5793-781X
AD  - Department of Chemistry, Universitat de les Illes Balears, Palma de Mallorca 
      07122, Spain.
FAU - Frontera, Antonio
AU  - Frontera A
AUID- ORCID: 0000-0001-7840-2139
AD  - Department of Chemistry, Universitat de les Illes Balears, Palma de Mallorca 
      07122, Spain.
FAU - Weigand, Jan J
AU  - Weigand JJ
AUID- ORCID: 0000-0001-7323-7816
AD  - Faculty of Chemistry and Food Chemistry, Technische Universitat Dresden, Dresden 
      01062, Germany.
LA  - eng
PT  - Journal Article
DEP - 20200515
PL  - United States
TA  - J Org Chem
JT  - The Journal of organic chemistry
JID - 2985193R
SB  - IM
EDAT- 2020/05/01 06:00
MHDA- 2020/05/01 06:01
CRDT- 2020/05/01 06:00
PHST- 2020/05/01 06:00 [pubmed]
PHST- 2020/05/01 06:01 [medline]
PHST- 2020/05/01 06:00 [entrez]
AID - 10.1021/acs.joc.0c00577 [doi]
PST - ppublish
SO  - J Org Chem. 2020 Nov 20;85(22):14420-14434. doi: 10.1021/acs.joc.0c00577. Epub 
      2020 May 15.