Concepedia

Arene CHO Hydrogen Bonding: A Stereocontrolling Tool in Palladium‐Catalyzed Arylation and Vinylation of Ketones

Zhiyan Huang, Li Hui Lim, Zuliang Chen, Yongxin Li, Feng Zhou, Haibin Su, Jianrong Steve Zhou

Angewandte Chemie International Edition · 2013 · 99 citations · 43 references

DOI

Concepts

Abstract

Weak is powerful: For the arylation of tin enolates, the palladium catalyst engages in weak CHO hydrogen bonds to control stereoselectivity (see scheme). Similar catalysts capable of NHO hydrogen bonding also works well.

References

43

The C−H···O Hydrogen Bond:  Structural Implications and Supramolecular Design

Gautam R. Desiraju · Accounts of Chemical Research · 1996 · 1.9K citations

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Palladium-Catalyzed α-Arylation of Carbonyl Compounds and Nitriles

Darcy A. Culkin, John F. Hartwig · Accounts of Chemical Research · 2003 · 934 citations

, , +12

Improved Catalysts for the Palladium-Catalyzed Synthesis of Oxindoles by Amide α-Arylation. Rate Acceleration, Use of Aryl Chloride Substrates, and a New Carbene Ligand for Asymmetric Transformations

Sunwoo Lee, John F. Hartwig · The Journal of Organic Chemistry · 2001 · 526 citations

, , +16

New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method

Iwao Ojima, Ivan Habuš, Mangzhu Zhao et al. · Tetrahedron · 1992 · 318 citations

, , +8

Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis

Anna Allen, David W. C. MacMillan · Journal of the American Chemical Society · 2011 · 310 citations

, , +11