Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds

Asymmetric enamine catalysis.

3.1. C-M and X-H as Nucleophiles 1806 3.2. C-H and X-M as Nucleophiles 1809 3.2.1. C-Halogen Bond Formations 1809 3.2.2. C-O Bond Formations 1812 3.3. C-H and X-H as Nucleophiles 1812 3.3.1. C-O Bond Formations 1812 3.3.2. C-N Bond Formations 1815 4. Oxidative X-X Bond Formations between Two Nucleophiles 1819 5. Conclusions 1819 Author Information 1819 Biographies 1819 Acknowledgment 1820 References 1820

Bond Formations between Two Nucleophiles: Transition Metal Catalyzed Oxidative Cross-Coupling Reactions

Over the last decade, substantial research has led to the introduction of an impressive number of efficient procedures which allow the selective construction of CC bonds by directly connecting two different CH bonds under oxidative conditions. Common to these methodologies is the generation of the reactive intermediates in situ by activation of both CH bonds. This strategy was introduced by the group of Li as cross-dehydrogenative coupling (CDC) and discloses waste-minimized synthetic alternatives to classic coupling procedures which rely on the use of prefunctionalized starting materials. This Review highlights the recent progress in the field of cross-dehydrogenative C sp 3C formations and provides a comprehensive overview on existing procedures and employed methodologies.

The Cross-Dehydrogenative Coupling of C sp 3H Bonds: A Versatile Strategy for CC Bond Formations

Complete Field Guide to Asymmetric BINOL-Phosphate Derived Brønsted Acid and Metal Catalysis: History and Classification by Mode of Activation; Brønsted Acidity, Hydrogen Bonding, Ion Pairing, and Metal Phosphates

Over the past decade, the combination of chiral phosphoric acid and palladium catalysis has emerged as a robust strategy to accomplish the regio-, and stereoselective functionalization of inactive C-H bonds, enabling the access to various types of chirality (central, planar and axial). This review article describes the origin of and advances in asymmetric functionalization of allylic C-H bonds, C(sp2)-H bonds and C(sp3)-H bonds enabled by chiral phosphoric acid and palladium combined catalysis.

Asymmetric C-H Functionalization Enabled by Pd/Chiral Phosphoric Acid Combined Catalysis

(R)-(+)-2,2′-Bis(methoxymethoxy)-1,1′-binaphthyl n-Butyllithium




Iodine 9-Phenanthreneboronic acid




Tetrakis(triphenylphosphine) palladium(0)




Phosphorus oxychloridea (R)-2,2′-Bis(methoxymethoxy)-3,3′-diiodo-1,1′- binaphthalene (R)-2,2′-Bis(methoxymethoxy)-3,3′-bis(9-phenanthryl)-1,1′-binaphthalene (R)-3,3′-Bis(9-phenanthryl)-1,1′-binaphthalene-2,2′-diol (R)-3,3′-Bis(9-phenanthryl)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate





Keywords:

3,3′-bis(9-phenanthryl)-1,1′-binaphthalene-2,2′-diyl hydrogen phosphate;
chiral Bronsted acid;
electrophiles;
protonation;
BINOL phosphates;
aza Diels-Alder reactions

(R)‐3,3′‐bis(9‐Phenanthryl)‐1,1′‐Binaphthalene‐2,2′‐Diyl Hydrogen Phosphate

Counteranion-Controlled Regioselectivity in Palladium-Catalyzed Allylic Amination of Dienyl Allylic Carbonates

The direct functionalization of allylic C–H bonds is distinguished by enabling rapid assembly of structural complexity from simple molecules. Although Pd-catalyzed allylic C–H functionalization has...

https://www.chinesechemsoc.org/doi/pdf/10.31635/ccschem.021.202100884

Liu-Zhu Gong

Papers

Asymmetric C-H Functionalization Enabled by Pd/Chiral Phosphoric Acid Combined Catalysis

(R)‐3,3′‐bis(9‐Phenanthryl)‐1,1′‐Binaphthalene‐2,2′‐Diyl Hydrogen Phosphate

Counteranion-Controlled Regioselectivity in Palladium-Catalyzed Allylic Amination of Dienyl Allylic Carbonates

Platinum-Catalyzed Allylic C–H Alkylation with Malononitriles

Einsatz von Wasserstoff bei der asymmetrischen organokatalytischen Hydrierung mithilfe der Staffelkatalyse