Probing the Limits of Oxidative Addition of C(sp3)-X Bonds toward Selected N,C,N-Chelated Bismuth(I) Compounds

被引:29
作者
Hejda, Martin [1 ]
Jirasko, Robert [2 ]
Ruzicka, Ales [1 ]
Jambor, Roman [1 ]
Dostal, Libor [1 ]
机构
[1] Univ Pardubice, Dept Gen & Inorgan Chem, CZ-53210 Pardubice, Czech Republic
[2] Univ Pardubice, Dept Analyt Chem, CZ-53210 Pardubice, Czech Republic
关键词
ORGANOBISMUTH(I) COMPOUND; LIGAND; COORDINATION; BI;
D O I
10.1021/acs.organomet.0c00418
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reactivity of two N,C,N-chelated bismuthinidenes, that is, [2,6- (tBuN=CH)(2)C6H3]Bi (1) and its metastable analogue [2,6-(Me2NCH2)(2)C6H3]Bi (2), toward organic substrates containing C(sp(3))-X bond (where X = I or OTf) is reported. The aim of this study is to prove the potential of the Bi(I) center in 1 and 2 to participate in an oxidative addition toward C-X bonds under formation of corresponding trivalent bismuth compounds. The influence of the substrate is examined; thus, simple primary alkyls (including fluorinated ones) as well as more branched substrates are considered to find the limits of these reactions and recognize the differences in the reactivity between 1 and 2. All products were characterized by means of high-resolution electrospray ionization mass spectrometry (ESI-MS); H-1, C-13, and F-19 NMR spectroscopy; and single-crystal X-ray diffraction analysis.
引用
收藏
页码:4320 / 4328
页数:9
相关论文
共 30 条
[11]   Coordination-Like Chemistry of Phosphinidenes by Phosphanes [J].
Protasiewicz, John D. .
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (29) :4539-4549
[12]   RELATIVISTIC EFFECTS IN STRUCTURAL CHEMISTRY [J].
PYYKKO, P .
CHEMICAL REVIEWS, 1988, 88 (03) :563-594
[13]   Molecular Single-Bond Covalent Radii for Elements 1-118 [J].
Pyykko, Pekka ;
Atsumi, Michiko .
CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (01) :186-197
[14]  
Sheldrick GM, 2015, ACTA CRYSTALLOGR C, V71, P3, DOI [10.1107/S2053273314026370, 10.1107/S2053229614024218, 10.1107/S0108767307043930]
[15]   Oxidative addition of organic disulfides to low valent N,C,N-chelated organobismuth(I) compound: Isolation, structure and coordination capability of substituted bismuth(III) bis(arylsulfides) [J].
Simon, Petr ;
Jambor, Roman ;
Ruzicka, Ales ;
Dostal, Libor .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 740 :98-103
[16]   Oxidative Addition of Diphenyldichalcogenides PhEEPh (E = S, Se, Te) to Low-Valent CN- and NCN-Chelated Organoantimony and Organobismuth Compounds [J].
Simon, Petr ;
Jambor, Roman ;
Ruzicka, Ales ;
Dostal, Libor .
ORGANOMETALLICS, 2013, 32 (01) :239-248
[17]   Monomeric Organoantimony(I) and Organobismuth(I) Compounds Stabilized by an NCN Chelating Ligand: Syntheses and Structures [J].
Simon, Petr ;
de Proft, Frank ;
Jambor, Roman ;
Ruzicka, Ales ;
Dostal, Libor .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) :5468-5471
[18]   Organobismuth(III) dihalides with T-shaped geometry stabilized by intramolecular N→Bi interactions and related diorganobismuth(III) halides [J].
Soran, Albert P. ;
Silvestru, Cristian ;
Breunig, Hans J. ;
Balazs, Gabor ;
Green, Jennifer C. .
ORGANOMETALLICS, 2007, 26 (05) :1196-1203
[19]   BYPASS - AN EFFECTIVE METHOD FOR THE REFINEMENT OF CRYSTAL-STRUCTURES CONTAINING DISORDERED SOLVENT REGIONS [J].
VANDERSLUIS, P ;
SPEK, AL .
ACTA CRYSTALLOGRAPHICA SECTION A, 1990, 46 :194-201
[20]   Trapping of the N,C,N-chelated organobismuth(I) compound, [2,6-(Me2NCH2)2C6H3] Bi, by its coordination toward selected transition metal fragments [J].
Vranova, Iva ;
Duskova, Tereza ;
Erben, Milan ;
Jambor, Roman ;
Ruzicka, Ales ;
Dostal, Libor .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2018, 863 :15-20