Cleavage of Carbon−Carbon Bonds of Diphenylacetylene and Its Derivatives via Photolysis of Pt Complexes:  Tuning the C−C Bond Formation Energy toward Selective C−C Bond Activation

2007 ◽  
Vol 129 (28) ◽  
pp. 8729-8735 ◽  
Author(s):  
Ahmet Gunay ◽  
William D. Jones
Keyword(s):  
Formation Energy ◽  
Bond Activation ◽  
Bond Formation ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

scholarly journals Metal-free visible light photoredox enables generation of carbyne equivalents via phosphonium ylide C–H activation

2019 ◽  
Vol 10 (6) ◽  
pp. 1687-1691 ◽  
Author(s):  
Mrinmoy Das ◽  
Minh Duy Vu ◽  
Qi Zhang ◽  
Xue-Wei Liu
Keyword(s):  
Visible Light ◽  
Bond Formation ◽  
Formation Processes ◽  
New Approach ◽  
Carbon Bond ◽  
Metal Free ◽  
Carbon Carbon Bond ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
New Strategy

Phosphonium ylides have shown their synthetic usefulness in important carbon–carbon bond formation processes. Our new strategy employs phosphonium ylides as novel carbyne equivalents and features a new approach for constructing carbon–carbon bonds from alkenes.

Palladium-catalyzed [2+1+1] annulation of norbornenes with (z)-bromostyrenes: synthesis of bismethylenecyclobutanes via twofold C(sp2)–H bond activation

2014 ◽  
Vol 50 (99) ◽  
pp. 15726-15729 ◽  
Author(s):  
Jiangang Mao ◽  
Weiliang Bao
Keyword(s):  
Bond Activation ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Palladium Catalyzed

A Pd(0)-catalyzed domino bismethylenecyclobutanation reaction was established. The [2+1+1] cycloaddition involves twofold C(sp2)–H bond activation and formation of three carbon–carbon bonds.

scholarly journals Direct activation of relatively unstrained carbon–carbon bonds in homogeneous systems

2014 ◽  
Vol 1 (5) ◽  
pp. 567-581 ◽  
Author(s):  
Alpay Dermenci ◽  
Jotham W. Coe ◽  
Guangbin Dong
Keyword(s):  
Bond Activation ◽  
State Of The Art ◽  
Carbon Bond ◽  
Homogeneous Systems ◽  
Direct Activation ◽  
Carbon Carbon Bond ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds ◽  
Art Methods

This review highlights the frontier of carbon–carbon bond activation and discusses state-of-the-art methods for activating relatively unstrained bonds in homogeneous systems.

Multiple Carbon Bond Formation Via the Radical Cyclization of Cycloalkenol Acetals. Application to trans Hydrindan Steroid Precursors

1992 ◽  
Vol 45 (1) ◽  
pp. 275 ◽  
Author(s):  
G Stork ◽  
PJ Franklin
Keyword(s):  
Double Bond ◽  
Bond Formation ◽  
Carbon Chain ◽  
Radical Cyclization ◽  
Carbon Bond ◽  
Single Operation ◽  
Carbon Carbon Bonds ◽  
Carbon Bonds

The cyclization of the α-iodo mixed acetals derived from properly substituted cyclohexenols , a process which has already been shown to permit the stereoselective and regioselective introduction of a different carbon chain at each of the termini of the allylic double bond, may be used for the construction of trans hydrindans suitable for further elaboration to steroids. In one particular instance, the process involves the formation of four new carbon-carbon bonds in a single operation.

Imine as a Linchpin Approach for Distal C(sp2)–H Functionalization

2020 ◽  
Author(s):  
Sukdev Bag ◽  
Sadhan Jana ◽  
Sukumar Pradhan ◽  
Suman Bhowmick ◽  
Nupur Goswami ◽  
...  
Keyword(s):  
Organic Molecules ◽  
Bond Activation ◽  
Bond Formation ◽  
Ancillary Ligand ◽  
Significant Challenge ◽  
Site Selectivity ◽  
Directing Group ◽  
Covalently Linked ◽  
Complex Organic ◽  
Post Functionalization

<p>Despite the widespread applications of C–H functionalization, controlling site selectivity remains a significant challenge. Covalently attached directing group (DG) served as an ancillary ligand to ensure proximal <i>ortho</i>-, distal <i>meta</i>- and <i>para</i>-C-H functionalization over the last two decades. These covalently linked DGs necessitate two extra steps for a single C–H functionalization: introduction of DG prior to C–H activation and removal of DG post-functionalization. We introduce here a transient directing group for distal C(<i>sp<sup>2</sup></i>)-H functionalization <i>via</i> reversible imine formation. By overruling facile proximal C-H bond activation by imine-<i>N</i> atom, a suitably designed pyrimidine-based transient directing group (TDG) successfully delivered selective distal C-C bond formation. Application of this transient directing group strategy for streamlining the synthesis of complex organic molecules without any necessary pre-functionalization at the distal position has been explored.</p>

Carbon Dioxide-Mediated C(sp2)–H Arylation of Primary and Secondary Benzylamines

2018 ◽  
Author(s):  
Mohit Kapoor ◽  
Pratibha Chand-Thakuri ◽  
Michael Young
Keyword(s):  
Carbon Dioxide ◽  
Transition Metal ◽  
Bond Activation ◽  
Bond Formation ◽  
Carbon Bond ◽  
Chelate Effect ◽  
Free Amine ◽  
Carbon Carbon Bond ◽  
New Strategy ◽  
Metal Catalyzed

Carbon-carbon bond formation by transition metal-catalyzed C–H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of <i>ortho</i>-arylbenzylamines, however, effective <i>ortho</i>-C–C bond formation from C–H bond activation of free primary and secondary benzylamines using Pd<sup>II</sup> remains an outstanding challenge. Presented herein is a new strategy for constructing <i>ortho</i>-arylated primary and secondary benzylamines mediated by carbon dioxide (CO<sub>2</sub>). The use of CO<sub>2</sub> is critical to allowing this transformation to proceed under milder conditions than previously reported, and that are necessary to furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, a chelate effect is demonstrated to facilitate selective monoarylation.

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