Unsymmetrical Difunctionalization of Two Different C–H Bonds in One Pot Under Transition-Metal Catalysis

Masahito Murai; Kazuhiko Takai

doi:10.1055/s-0037-1611066

Synthesis, Table of Contents

CC BY ND NC 4.0 · Synthesis 2019; 51(01): 40-54
DOI: 10.1055/s-0037-1611066

short review

Copyright with the author

Unsymmetrical Difunctionalization of Two Different C–H Bonds in One Pot Under Transition-Metal Catalysis

Masahito Murai *

Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan Email: masahito.murai@okayama-u.ac.jp Email: ktakai@cc.okayama-u.ac.jp

,

Kazuhiko Takai *

Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan Email: masahito.murai@okayama-u.ac.jp Email: ktakai@cc.okayama-u.ac.jp

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Abstract

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Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue

Abstract

Recent advancements in unsymmetrical difunctionalization based on the substitution of two different C–H bonds in one-pot are described. Due to the difficulty of controlling reactivity and selectivity, multi-functionalization via substitution of several C–H bonds to install different functional groups has been limited until recently, in comparison with well-studied functionalization via sequential addition to unsaturated π-bonds. This difunctionalization protocol provides an efficient and rapid approach to a library of structurally complicated target molecules through the formation of multiple C–X bonds with high atom- and step-economy.

1 Introduction

2 ortho-Selective Functionalization of Two Different C–H Bonds Relative to the Directing Group

2.1 Unsymmetrical Difunctionalization with the Introduction of Similar Functional Groups

2.2 Unsymmetrical Difunctionalization with the Introduction of Different Functional Groups

2.3 ortho-Selective Unsymmetrical Difunctionalization Promoted by Two Different Directing Groups Appearing During the Progress of the Reaction

3 ortho/meta-Selective C–H Bond Difunctionalization Relative to the Directing Group

4 Sequential Difunctionalization of Fused Aromatic Compounds and Heterocycles

5 Summary and Outlook

Key words

difunctionalization - C–H activation - regioselectivity

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References

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