Home / Publications / Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes

Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes

Sergey Aleksandrovich Rzhevskiy 1
Sergey Aleksandrovich Rzhevskiy
,  , 
Yulia D Golenko 1
Yulia D Golenko
,  , 
Grigorii Konstantinovich Sterligov 1, 3
Grigorii Konstantinovich Sterligov
, 
Nikita Yuryevich Kirilenko 1, 3
Nikita Yuryevich Kirilenko
, 
Alexandra Andreevna Ageshina 1
Alexandra Andreevna Ageshina
, 
Maksim Vladimirovich Bermeshev 1
Maksim Vladimirovich Bermeshev
,  , 
Andrey Fedorovich Asachenko 1, 2
Andrey Fedorovich Asachenko
10.1016/j.mencom.2020.09.005
Published 2020-08-31
Communication , Volume 30, Issue 5, 569-571
6
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Rzhevskiy S. A. et al. Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 569-571.
GOST all authors (up to 50) Copy
Rzhevskiy S. A., Topchiy M. A., Golenko Y. D., Gribanov P. S., Sterligov G. K., Kirilenko N. Y., Ageshina A. A., Bermeshev M. V., Nechaev M. S., Asachenko A. F. Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 569-571.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.09.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.005
TI - Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes
T2 - Mendeleev Communications
AU - Rzhevskiy, Sergey Aleksandrovich
AU - Topchiy, Maxim Anatol'evich
AU - Golenko, Yulia D
AU - Gribanov, Pavel Sergeevich
AU - Sterligov, Grigorii Konstantinovich
AU - Kirilenko, Nikita Yuryevich
AU - Ageshina, Alexandra Andreevna
AU - Bermeshev, Maksim Vladimirovich
AU - Nechaev, M S
AU - Asachenko, Andrey Fedorovich
PY - 2020
DA - 2020/08/31
PB - Mendeleev Communications
SP - 569-571
IS - 5
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Rzhevskiy,
author = {Sergey Aleksandrovich Rzhevskiy and Maxim Anatol'evich Topchiy and Yulia D Golenko and Pavel Sergeevich Gribanov and Grigorii Konstantinovich Sterligov and Nikita Yuryevich Kirilenko and Alexandra Andreevna Ageshina and Maksim Vladimirovich Bermeshev and M S Nechaev and Andrey Fedorovich Asachenko},
title = {Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.005},
number = {5},
pages = {569--571},
doi = {10.1016/j.mencom.2020.09.005}
}
MLA
Cite this
MLA Copy
Rzhevskiy, Sergey Aleksandrovich, et al. “Undirected ortho-selectivity in C–H borylation of arenes catalyzed by NHC platinum(0) complexes.” Mendeleev Communications, vol. 30, no. 5, Aug. 2020, pp. 569-571. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.005.

Keywords

N-heterocyclic carbenes
arenes
borylation
catalysis
organoboron compounds
platinum(0) complexes
regioselectivity

Abstract

Borylation of arenes with bis(pinacolato)diboron catalyzed by sterically encumbered NHC platinum complexes proceeds predominantly at ortho-position even in the absence of a directing group (o : m : p ratio up to 10: 3: 1). The similar borylation with pinacolborane would proceed less selectively.

References

2.
Platinum-catalyzed Aromatic C–H Silylation of Arenes with 1,1,1,3,5,5,5-Heptamethyltrisiloxane
Murata M., Fukuyama N., Wada J., Watanabe S., Masuda Y.
Chemistry Letters, 2007
3.
Lukin R.Y., Emelyanov D.A., Kachmarzhik A.D., Sukhov A.V., Sinyashin O.G., Yakhvarov D.G.
Mendeleev Communications, 2019
5.
Diboron(4) Compounds: From Structural Curiosity to Synthetic Workhorse
Neeve E.C., Geier S.J., Mkhalid I.A., Westcott S.A., Marder T.B.
Chemical Reviews, 2016
6.
Catalytic, Direct Synthesis of Bis(boronate) Compounds
Takaya J., Iwasawa N.
ACS Catalysis, 2012
8.
Perceptible Influence of Pd and Pt Heterocyclic Carbene-Pyridyl Complexes in Catalytic Diboration of Cyclic Alkenes
Pubill-Ulldemolins C., Bo C., Mata J., Fernández E.
Chemistry - An Asian Journal, 2010
9.
Fluorine-controlled C–H borylation of arenes catalyzed by a PSiN-pincer platinum complex
Takaya J., Ito S., Nomoto H., Saito N., Kirai N., Iwasawa N.
Chemical Communications, 2015
10.
C–H Functionalization at Sterically Congested Positions by the Platinum-Catalyzed Borylation of Arenes
Furukawa T., Tobisu M., Chatani N.
Journal of the American Chemical Society, 2015
11.
C–H Borylation by Platinum Catalysis
Furukawa T., Tobisu M., Chatani N.
Bulletin of the Chemical Society of Japan, 2017
13.
Regio- and stereoselective dimerization of arylacetylenes and optical and electrochemical studies of (E)-1,3-enynes
Morozov O.S., Asachenko A.F., Antonov D.V., Kochurov V.S., Paraschuk D.Y., Nechaev M.S.
Advanced Synthesis and Catalysis, 2014
14.
Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes
Topchiy M.A., Dzhevakov P.B., Rubina M.S., Morozov O.S., Asachenko A.F., Nechaev M.S.
European Journal of Organic Chemistry, 2016
15.
Mixed er-NHC/phosphine Pd(ii) complexes and their catalytic activity in the Buchwald–Hartwig reaction under solvent-free conditions
Ageshina A.A., Sterligov G.K., Rzhevskiy S.A., Topchiy M.A., Chesnokov G.A., Gribanov P.S., Melnikova E.K., Nechaev M.S., Asachenko A.F., Bermeshev M.V.
Dalton Transactions, 2019
16.
Hydrohydrazination of Arylalkynes Catalyzed by an Expanded Ring N-Heterocyclic Carbene (er-NHC) Gold Complex under Solvent-Free Conditions
Morozov O.S., Gribanov P.S., Asachenko A.F., Dorovatovskii P.V., Khrustalev V.N., Rybakov V.B., Nechaev M.S.
Advanced Synthesis and Catalysis, 2016
18.
Alkynyl‐ or Azido‐Functionalized 1,2,3‐Triazoles: Selective MonoCuAAC Promoted by Physical Factors
Topchiy M.A., Ageshina A.A., Chesnokov G.A., Sterligov G.K., Rzhevskiy S.A., Gribanov P.S., Osipov S.N., Nechaev M.S., Asachenko A.F.
ChemistrySelect, 2019
19.
Azide-Alkyne Cycloaddition (CuAAC) in Alkane Solvents Catalyzed by Fluorinated NHC Copper(I) Complex
Topchiy M.A., Ageshina A.A., Gribanov P.S., Masoud S.M., Akmalov T.R., Nefedov S.E., Osipov S.N., Nechaev M.S., Asachenko A.F.
European Journal of Organic Chemistry, 2018
20.
New expanded-ring NHC platinum(0) complexes: Synthesis, structure and highly efficient diboration of terminal alkenes
Rzhevskiy S.A., Topchiy M.A., Lyssenko K.A., Philippova A.N., Belaya M.A., Ageshina A.A., Bermeshev M.V., Nechaev M.S., Asachenko A.F.
Journal of Organometallic Chemistry, 2020
21.
10.1016/j.mencom.2020.09.005_bib0040
Choi
Iridium Catalysis, 2011