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

来源：

ORGANOMETALLICS | 2020年 / 39卷 / 23期

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

页码：4320 / 4328

页数：9

共 30 条

[1] USE OF THE 2,6-BIS[(DIMETHYLAMINO)METHYL]PHENYL LIGAND TO FORM SOME PENTACOORDINATE DERIVATIVES OF P(III), AS(III), SB(III) AND BI(III) [J].

ATWOOD, DA ;

COWLEY, AH ;

RUIZ, J .

INORGANICA CHIMICA ACTA, 1992, 198 :271-274

[2] Oxidative Addition and Reductive Elimination at Main-Group Element Centers [J].

Chu, Terry ;

Nikonov, Georgii I. .

CHEMICAL REVIEWS, 2018, 118 (07) :3608-3680

[3] N-Heterocyclic Carbene Adducts of Main Group Elements and Their Use as Ligands in Transition Metal Chemistry [J].

Doddi, Adinarayana ;

Peters, Marius ;

Tamm, Matthias .

CHEMICAL REVIEWS, 2019, 119 (12) :6994-7112

[4] Quest for stable or masked pnictinidenes: Emerging and exciting class of group 15 compounds [J].

Dostal, Libor .

COORDINATION CHEMISTRY REVIEWS, 2017, 353 :142-158

[5] STRUCTURAL ANALYSIS OF ORGANOMETALLIC COMPOUNDS WITH SOFT IONIZATION MASS SPECTROMETRY [J].

Jirasko, Robert ;

Holcapek, Michal .

MASS SPECTROMETRY REVIEWS, 2011, 30 (06) :1013-1036

[6] A Redox-Confused Bismuth(I/III) Triamide with a T-Shaped Planar Ground State [J].

Kindervater, Marcus B. ;

Marczenko, Katherine M. ;

Werner-Zwanziger, Ulrike ;

Chitnis, Saurabh S. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (23) :7850-7855

[7] Hetero Diels-Alder Reactions of Masked Dienes Containing Heavy Group 15 Elements [J].

Korenkova, Monika ;

Kremlacek, Vit ;

Hejda, Martin ;

Turek, Jan ;

Khudaverdyan, Raffi ;

Erben, Milan ;

Jambor, Roman ;

Ruzicka, Ales ;

Dostal, Libor .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (05) :1144-1154

[8] N-Heterocyclic Carbene-Phosphinidene Adducts: Synthesis, Properties, and Applications [J].

Krachko, Tetiana ;

Slootweg, J. Chris .

EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (24) :2734-2754

[9] A Singlet Phosphinidene Stable at Room Temperature [J].

Liu, Liu ;

Ruiz, David A. ;

Munz, Dominik ;

Bertrand, Guy .

CHEM, 2016, 1 (01) :147-153

[10] NHCs in Main Group Chemistry [J].

Nesterov, Vitaly ;

Reiter, Dominik ;

Bag, Prasenjit ;

Frisch, Philipp ;

Holzner, Richard ;

Porzelt, Amelie ;

Inoue, Shigeyoshi .

CHEMICAL REVIEWS, 2018, 118 (19) :9678-9842

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