Unraveling innate substrate control in site-selective palladium-catalyzed C–H heterocycle functionalization-Reference-Cited by-同舟云学术

Unraveling innate substrate control in site-selective palladium-catalyzed C–H heterocycle functionalization

Published:2016 Issue:6 Volume:7 Page:3900-3909
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Choi Hwanho¹²³⁴⁵,Min Minsik⁶⁷⁸⁹²,Peng Qian¹²³⁴⁵,Kang Dahye⁶⁷⁸⁹²,Paton Robert S.¹²³⁴⁵,Hong Sungwoo⁶⁷⁸⁹²

Affiliation:

1. Chemistry Research Laboratory

2. Department of Chemistry

3. University of Oxford

4. Oxford OX1 3TA

5. UK

6. Center for Catalytic Hydrocarbon Functionalizations

7. Institute for Basic Science (IBS)

8. Daejeon

9. 34141 Korea

Abstract

Pd(ii)-catalyzed direct arylation of chromones and enaminones gives divergent site-selectivities. Computational and experimental studies reveal a switch in mechanism, from a C3-selective CMD mechanism to a C2-selective carbopalladation pathway. This model accounts for the opposite selectivities of enaminone and chromone, and also correctly predicts selectivities for the C–H functionalization of heteroaromatic substrates as a function of the coupling partner.

Funder

Royal Society

European Commission

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2016/SC/C5SC04590H

Reference105 articles.

1. Palladium- and Copper-Catalyzed Arylation of Carbon−Hydrogen Bonds

2. Palladium(II)-Catalyzed CH Activation/CC Cross-Coupling Reactions: Versatility and Practicality