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

Nature Chemistry
Xiangqing Jia, Zheng Huang

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.

References

May 31, 2002·Nature·Jay A Labinger, John E Bercaw
Apr 16, 2003·Accounts of Chemical Research·Stephen J Blanksby, G Barney Ellison
Mar 23, 2007·Nature·Robert G Bergman
Sep 23, 2009·Chemical Reviews·Paul R Ortiz de Montellano
Mar 12, 2011·Chemical Reviews·Jongwook ChoiAlan S Goldman
May 22, 2013·Organic Letters·Jennifer V Obligacion, Paul J Chirik
May 16, 2014·Angewandte Chemie·Abhishek Dutta ChowdhuryMatthias Beller
Oct 3, 2015·Angewandte Chemie·Ivan BuslovXile Hu
Oct 8, 2015·Journal of the American Chemical Society·Chi ChenPatrick L Holland

❮ Previous
Next ❯

Citations

Jun 14, 2016·ACS Central Science·John F Hartwig, Matthew A Larsen
Jun 13, 2018·Angewandte Chemie·Jonathan R CarneyStephen P Thomas
Aug 31, 2016·Angewandte Chemie·Chen ChengJohn F Hartwig
Nov 30, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Christopher L Rock, Ryan J Trovitch
Dec 5, 2019·Angewandte Chemie·Jie LiWanxiang Zhao
Apr 26, 2016·Angewandte Chemie·Xiaoyong DuZheng Huang
Nov 26, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Ravi SrivastavaClément Camp
Jul 16, 2020·Angewandte Chemie·Leandro Duarte de AlmeidaMatthias Beller
Dec 16, 2020·Nature Chemistry·Jie DongJin Xie
Feb 26, 2021·Chemical Society Reviews·Bin Li, Pierre H Dixneuf
Oct 27, 2016·Angewandte Chemie·Stéphanie DupuyOlivier Baudoin
Aug 10, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Niroshani S AbeynayakeVirginia Montiel-Palma
Jul 27, 2017·Journal of the American Chemical Society·Huaquan FangZheng Huang
Mar 9, 2018·Journal of the American Chemical Society·Yulei WangZheng Huang
Sep 28, 2017·Chemical Reviews·Akshai KumarAlan S Goldman
Sep 16, 2016·Journal of the American Chemical Society·F Mark ChadwickAndrew S Weller
Mar 14, 2018·ACS Central Science·Heiko SommerIlan Marek
Mar 3, 2018·Journal of the American Chemical Society·Xinxin TangZheng Huang
Sep 29, 2021·Organic Letters·Yaqin LeiWanxiang Zhao
Sep 19, 2021·Chemistry, an Asian Journal·Katsuaki Kobayashi, Hiroshi Nakazawa
Oct 1, 2021·Journal of the American Chemical Society·Min-Jie ZhouZheng Huang
Oct 8, 2021·Chemical Reviews·Shubhankar Kumar BoseTodd B Marder
Dec 9, 2021·Angewandte Chemie·Tian FengYouai Qiu

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.