Rhodium(I)-Catalyzed Sequential C(sp)C(sp3) and C(sp3)C(sp3) Bond Formation through Migratory Carbene Insertion

2015 ◽  
Vol 127 (27) ◽  
pp. 8002-8005 ◽  
Author(s):  
Ying Xia ◽  
Sheng Feng ◽  
Zhen Liu ◽  
Yan Zhang ◽  
Jianbo Wang
Keyword(s):  
Bond Formation ◽  
Carbene Insertion

ChemInform Abstract: Rhodium(I)-Catalyzed Sequential C(sp)-C(sp3) and C(sp3)-C(sp3) Bond Formation Through Migratory Carbene Insertion.

ChemInform ◽  
2015 ◽  
Vol 46 (43) ◽  
pp. no-no
Author(s):  
Ying Xia ◽  
Sheng Feng ◽  
Zhen Liu ◽  
Yan Zhang ◽  
Jianbo Wang
Keyword(s):  
Bond Formation ◽  
Carbene Insertion

CN bond formation via palladium-catalyzed carbene insertion into NN bonds: inhibiting the general 1,2-migration process of ylide intermediates

2017 ◽  
Vol 53 (18) ◽  
pp. 2697-2700 ◽  
Author(s):  
Chuanle Zhu ◽  
Pengquan Chen ◽  
Rui Zhu ◽  
Zhiming Lin ◽  
Wanqing Wu ◽  
...  
Keyword(s):  
Bond Formation ◽  
Migration Process ◽  
Carbene Insertion ◽  
Palladium Catalyzed

Inhibiting the general 1,2-migration process of ylide intermediates, a new palladium-catalyzed carbene insertion into NN bonds affords various N,N-disubstituted hydrazones.

Carbene insertion into transition metal–carbon bonds: a new tool for catalytic C–C bond formation

2011 ◽  
Vol 1 (2) ◽  
pp. 153 ◽  
Author(s):  
Nicole M. G. Franssen ◽  
Annemarie J. C. Walters ◽  
Joost N. H. Reek ◽  
Bas de Bruin
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Carbene Insertion ◽  
Carbon Bonds

Palladium(0)-catalyzed C(sp3)–Si bond formation via formal carbene insertion into a Si–H bond

2018 ◽  
Vol 54 (81) ◽  
pp. 11419-11422 ◽  
Author(s):  
Zhenxing Liu ◽  
Jingfeng Huo ◽  
Tianren Fu ◽  
Haocheng Tan ◽  
Fei Ye ◽  
...  
Keyword(s):  
Efficient Method ◽  
Bond Formation ◽  
Carbene Insertion

Pd(0)-Catalyzed formal carbene insertion into Si–H bonds has been achieved as an efficient method for C(sp3)–Si bond formation.

scholarly journals Origin and Control of Chemoselectivity in Cytochrome c-Catalyzed Carbene Transfer into Si–H and N–H bonds

2021 ◽  
Author(s):  
Marc Garcia-Borràs ◽  
S. B. Jennifer Kan ◽  
Russell D. Lewis ◽  
Allison Tang ◽  
Gonzalo Jiménez-Osés ◽  
...  
Keyword(s):  
Cytochrome C ◽  
Bond Formation ◽  
Conformational Dynamics ◽  
Active Species ◽  
Chemical Transformations ◽  
Carbene Insertion ◽  
Biological World ◽  
Selective Chemical ◽  
And Control ◽  
Loop Conformation

<div><div><div><p>A cytochrome c heme protein was recently engineered to catalyze the formation of carbon–silicon bonds via carbene insertion into Si–H bonds, a reaction that was not previously known to be catalyzed by a protein. High chemoselectivity towards C–Si bond formation over competing C–N bond formation was achieved, although this trait was not screened for during directed evolution. Using computational and experimental tools, we now establish that activity and chemoselectivity are modulated by conformational dynamics of a protein loop that covers the substrate access to the iron-carbene active species. Mutagenesis of residues computationally predicted to control the loop conformation altered the protein’s chemoselectivity from preferred silylation to preferred amination of a substrate containing both N–H and Si–H functionalities. We demonstrate that information on protein structure and conformational dynamics, combined with knowledge of mechanism, leads to understanding of how non-natural and selective chemical transformations can be introduced into the biological world.</p></div></div></div>

ChemInform Abstract: Carbene Insertion into Transition Metal-Carbon Bonds: A New Tool for Catalytic C-C Bond Formation.

ChemInform ◽  
2011 ◽  
Vol 42 (39) ◽  
pp. no-no
Author(s):  
Nicole M. G. Franssen ◽  
Annemarie J. C. Walters ◽  
Joost N. H. Reek ◽  
Bas de Bruin
Keyword(s):  
Transition Metal ◽  
Bond Formation ◽  
Carbene Insertion ◽  
Carbon Bonds

scholarly journals Origin and Control of Chemoselectivity in Cytochrome c-Catalyzed Carbene Transfer into Si–H and N–H bonds

2021 ◽  
Author(s):  
Marc Garcia-Borràs ◽  
S. B. Jennifer Kan ◽  
Russell D. Lewis ◽  
Allison Tang ◽  
Gonzalo Jiménez-Osés ◽  
...  
Keyword(s):  
Cytochrome C ◽  
Bond Formation ◽  
Conformational Dynamics ◽  
Active Species ◽  
Chemical Transformations ◽  
Carbene Insertion ◽  
Biological World ◽  
Selective Chemical ◽  
And Control ◽  
Loop Conformation

<div><div><div><p>A cytochrome c heme protein was recently engineered to catalyze the formation of carbon–silicon bonds via carbene insertion into Si–H bonds, a reaction that was not previously known to be catalyzed by a protein. High chemoselectivity towards C–Si bond formation over competing C–N bond formation was achieved, although this trait was not screened for during directed evolution. Using computational and experimental tools, we now establish that activity and chemoselectivity are modulated by conformational dynamics of a protein loop that covers the substrate access to the iron-carbene active species. Mutagenesis of residues computationally predicted to control the loop conformation altered the protein’s chemoselectivity from preferred silylation to preferred amination of a substrate containing both N–H and Si–H functionalities. We demonstrate that information on protein structure and conformational dynamics, combined with knowledge of mechanism, leads to understanding of how non-natural and selective chemical transformations can be introduced into the biological world.</p></div></div></div>

Rhodium(I)-Catalyzed Sequential C(sp)C(sp3) and C(sp3)C(sp3) Bond Formation through Migratory Carbene Insertion

2015 ◽  
Vol 54 (27) ◽  
pp. 7891-7894 ◽  
Author(s):  
Ying Xia ◽  
Sheng Feng ◽  
Zhen Liu ◽  
Yan Zhang ◽  
Jianbo Wang
Keyword(s):  
Bond Formation ◽  
Carbene Insertion
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