scholarly journals Recent progress in the catalytic carbene insertion reactions into the silicon–hydrogen bond

2017 ◽  
Vol 15 (26) ◽  
pp. 5441-5456 ◽  
Author(s):  
Hoda Keipour ◽  
Virginie Carreras ◽  
Thierry Ollevier
Keyword(s):  
Hydrogen Bond ◽  
Recent Progress ◽  
Insertion Reactions ◽  
Carbene Insertion ◽  
Metal Carbenes ◽  
Selective Formation

This account reviews the development of Si–H bond insertion reactions, giving an overview of the catalysts employed. Metal carbenes can be inserted into Si–H bonds, allowing the selective formation of C–Si bonds.

scholarly journals Selective Functionalization of Aliphatic Amines via Myoglobin-Catalyzed Carbene N–H Insertion

Synlett ◽  
2019 ◽  
Vol 31 (03) ◽  
pp. 224-229 ◽  
Author(s):  
Viktoria Steck ◽  
Gopeekrishnan Sreenilayam ◽  
Rudi Fasan
Keyword(s):  
Bioactive Compounds ◽  
High Efficiency ◽  
Aliphatic Amines ◽  
Transfer Reactions ◽  
Insertion Reactions ◽  
Selective Functionalization ◽  
Insertion Product ◽  
Carbene Insertion ◽  
Selective Formation ◽  
Single Insertion

Engineered myoglobins have recently gained attention for their ability to catalyze a variety of abiological carbene transfer reactions including the functionalization of amines via carbene insertion into N–H bonds. However, the scope of myoglobin and other hemoprotein-based biocatalysts in the context of this transformation has been largely limited to aniline derivatives as the amine substrates and ethyl diazoacetate as the carbene donor reagent. In this report, we describe the development of an engineered myoglobin-based catalyst that is useful for promoting carbene N–H insertion reactions across a broad range of substituted benzylamines and α-diazo acetates with high efficiency (82–99% conversion), elevated catalytic turnovers (up to 7,000), and excellent chemoselectivity for the desired single insertion product (up to 99%). The scope of this transformation could be extended to cyclic aliphatic amines. These studies expand the biocatalytic toolbox available for the selective formation of C–N bonds, which are ubiquitous in many natural and synthetic bioactive compounds.

scholarly journals Organocatalytic Asymmetric Synthesis of α-Amino Esters from Sulfoxonium Ylides

2021 ◽  
Author(s):  
Wengang Guo ◽  
Hai Huang ◽  
Jianwei Sun
Keyword(s):  
Asymmetric Synthesis ◽  
Insertion Reaction ◽  
Metal Catalyst ◽  
Insertion Reactions ◽  
Amino Esters ◽  
Carbene Insertion

Described here is the first organocatalytic asymmetric N−H insertion reaction of α-carbonyl sulfoxonium ylides. Without a metal catalyst, this reaction represents an attractive complement to the well-established carbene insertion reactions....

scholarly journals New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

2016 ◽  
Vol 12 ◽  
pp. 2834-2848 ◽  
Author(s):  
Pavel Nagorny ◽  
Zhankui Sun
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Recent Progress ◽  
Halogen Bonds ◽  
Hydrogen Bond Donor ◽  
New Approaches ◽  
Substrate Activation ◽  
Non Covalent Interactions ◽  
Covalent Interactions ◽  
Hydrogen Bond Donors

Hydrogen bond donor catalysis represents a rapidly growing subfield of organocatalysis. While traditional hydrogen bond donors containing N–H and O–H moieties have been effectively used for electrophile activation, activation based on other types of non-covalent interactions is less common. This mini review highlights recent progress in developing and exploring new organic catalysts for electrophile activation through the formation of C–H hydrogen bonds and C–X halogen bonds.

Engineering of RuMb: Toward a Green Catalyst for Carbene Insertion Reactions

2017 ◽  
Vol 56 (10) ◽  
pp. 5623-5635 ◽  
Author(s):  
Matthew W. Wolf ◽  
David A. Vargas ◽  
Nicolai Lehnert
Keyword(s):  
Insertion Reactions ◽  
Green Catalyst ◽  
Carbene Insertion

ChemInform Abstract: Tandem Michael-Carbene Insertion Reactions of Alkynyliodonium Salts. Extremely Efficient Cyclopentene Annulations.

ChemInform ◽  
1987 ◽  
Vol 18 (20) ◽  
Author(s):  
M. OCHIAI ◽  
M. KUNISHIMA ◽  
Y. NAGAO ◽  
K. FUJI ◽  
M. SHIRO ◽  
...  
Keyword(s):  
Insertion Reactions ◽  
Carbene Insertion

Synthesis of 2,5-dihydrofurans via alkylidene carbene insertion reactions

1998 ◽  
Vol 39 (29) ◽  
pp. 5273-5276 ◽  
Author(s):  
Louise F. Walker ◽  
Stephen Connolly ◽  
Martin Wills
Keyword(s):  
Insertion Reactions ◽  
Carbene Insertion ◽  
Alkylidene Carbene
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