Literature DB >> 26791899

Conversion of alkanes to linear alkylsilanes using an iridium-iron-catalysed tandem dehydrogenation-isomerization-hydrosilylation.

Xiangqing Jia1, Zheng Huang1.   

Abstract

The conversion of inexpensive, saturated hydrocarbon feedstocks into value-added speciality chemicals using regiospecific, catalytic functionalization of alkanes is a major goal of organometallic chemistry. Linear alkylsilanes represent one such speciality chemical-they have a wide range of applications, including release coatings, silicone rubbers and moulding products. Direct, selective, functionalization of alkanes at primary C-H bonds is difficult and, to date, methods for catalytically converting alkanes into linear alkylsilanes are unknown. Here, we report a well-defined, dual-catalyst system for one-pot, two-step alkane silylations. The system comprises a pincer-ligated Ir catalyst for alkane dehydrogenation and an Fe catalyst that effects a subsequent tandem olefin isomerization-hydrosilylation. This method exhibits exclusive regioselectivity for the production of terminally functionalized alkylsilanes. This dual-catalyst strategy has also been applied to regioselective alkane borylations to form linear alkylboronate esters.

Entities:  

Year:  2015        PMID: 26791899     DOI: 10.1038/nchem.2417

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  24 in total

1.  Oligomerization of ethylene to α-olefins: discovery and development of the shell higher olefin process (SHOP).

Authors:  Wilhelm Keim
Journal:  Angew Chem Int Ed Engl       Date:  2013-10-15       Impact factor: 15.336

2.  Intermolecular and intramolecular, platinum-catalyzed, acceptorless dehydrogenative coupling of hydrosilanes with aryl and aliphatic methyl C-H bonds.

Authors:  Naofumi Tsukada; John F Hartwig
Journal:  J Am Chem Soc       Date:  2005-04-13       Impact factor: 15.419

Review 3.  Advances in transition metal (Pd, Ni, Fe)-catalyzed cross-coupling reactions using alkyl-organometallics as reaction partners.

Authors:  Ranjan Jana; Tejas P Pathak; Matthew S Sigman
Journal:  Chem Rev       Date:  2011-02-14       Impact factor: 60.622

4.  Silver-catalyzed C-C bond formation between methane and ethyl diazoacetate in supercritical CO₂.

Authors:  Ana Caballero; Emmanuelle Despagnet-Ayoub; M Mar Díaz-Requejo; Alba Díaz-Rodríguez; María Elena González-Núñez; Rossella Mello; Bianca K Muñoz; Wilfried-Solo Ojo; Gregorio Asensio; Michel Etienne; Pedro J Pérez
Journal:  Science       Date:  2011-05-13       Impact factor: 47.728

Review 5.  Understanding and exploiting C-H bond activation.

Authors:  Jay A Labinger; John E Bercaw
Journal:  Nature       Date:  2002-05-30       Impact factor: 49.962

6.  Bis(imino)pyridine cobalt-catalyzed alkene isomerization-hydroboration: a strategy for remote hydrofunctionalization with terminal selectivity.

Authors:  Jennifer V Obligacion; Paul J Chirik
Journal:  J Am Chem Soc       Date:  2013-12-16       Impact factor: 15.419

Review 7.  Hydrocarbon hydroxylation by cytochrome P450 enzymes.

Authors:  Paul R Ortiz de Montellano
Journal:  Chem Rev       Date:  2010-02-10       Impact factor: 60.622

8.  Highly selective bis(imino)pyridine iron-catalyzed alkene hydroboration.

Authors:  Jennifer V Obligacion; Paul J Chirik
Journal:  Org Lett       Date:  2013-05-21       Impact factor: 6.005

9.  Highly regioselective functionalization of aliphatic carbon-hydrogen bonds with a perbromohomoscorpionate copper(I) catalyst.

Authors:  Ana Caballero; M Mar Díaz-Requejo; Tomás R Belderraín; M Carmen Nicasio; Swiatoslaw Trofimenko; Pedro J Pérez
Journal:  J Am Chem Soc       Date:  2003-02-12       Impact factor: 15.419

10.  Catalytic functionalization of unactivated primary C-H bonds directed by an alcohol.

Authors:  Eric M Simmons; John F Hartwig
Journal:  Nature       Date:  2012-02-29       Impact factor: 49.962

View more
  18 in total

1.  Manganese-catalysed divergent silylation of alkenes.

Authors:  Jie Dong; Xiang-Ai Yuan; Zhongfei Yan; Liying Mu; Junyang Ma; Chengjian Zhu; Jin Xie
Journal:  Nat Chem       Date:  2020-12-14       Impact factor: 24.427

Review 2.  Challenges and opportunities for alkane functionalisation using molecular catalysts.

Authors:  Xinxin Tang; Xiangqing Jia; Zheng Huang
Journal:  Chem Sci       Date:  2017-11-09       Impact factor: 9.825

Review 3.  Walking Metals for Remote Functionalization.

Authors:  Heiko Sommer; Francisco Juliá-Hernández; Ruben Martin; Ilan Marek
Journal:  ACS Cent Sci       Date:  2018-02-08       Impact factor: 14.553

4.  Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions.

Authors:  Xinxin Qi; Li-Bing Jiang; Chao Zhou; Jin-Bao Peng; Xiao-Feng Wu
Journal:  ChemistryOpen       Date:  2017-03-16       Impact factor: 2.911

5.  Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C-H borylation using counterion activated earth-abundant metal catalysis.

Authors:  Riaz Agahi; Amy J Challinor; Joanne Dunne; Jamie H Docherty; Neil B Carter; Stephen P Thomas
Journal:  Chem Sci       Date:  2019-04-08       Impact factor: 9.825

Review 6.  Undirected, Homogeneous C-H Bond Functionalization: Challenges and Opportunities.

Authors:  John F Hartwig; Matthew A Larsen
Journal:  ACS Cent Sci       Date:  2016-05-02       Impact factor: 14.553

7.  Ligands with 1,10-phenanthroline scaffold for highly regioselective iron-catalyzed alkene hydrosilylation.

Authors:  Meng-Yang Hu; Qiao He; Song-Jie Fan; Zi-Chen Wang; Luo-Yan Liu; Yi-Jiang Mu; Qian Peng; Shou-Fei Zhu
Journal:  Nat Commun       Date:  2018-01-15       Impact factor: 14.919

8.  Rapid reversible borane to boryl hydride exchange by metal shuttling on the carborane cluster surface.

Authors:  Bennett J Eleazer; Mark D Smith; Alexey A Popov; Dmitry V Peryshkov
Journal:  Chem Sci       Date:  2017-05-25       Impact factor: 9.825

9.  Asymmetric remote C-H borylation of internal alkenes via alkene isomerization.

Authors:  Xu Chen; Zhaoyang Cheng; Jun Guo; Zhan Lu
Journal:  Nat Commun       Date:  2018-09-26       Impact factor: 14.919

10.  A β-diketiminate manganese catalyst for alkene hydrosilylation: substrate scope, silicone preparation, and mechanistic insight.

Authors:  Tufan K Mukhopadhyay; Marco Flores; Thomas L Groy; Ryan J Trovitch
Journal:  Chem Sci       Date:  2018-08-15       Impact factor: 9.825

View more

北京卡尤迪生物科技股份有限公司 © 2022-2023.