Synthesis of tetrasubstituted allenes via a 1,4-palladium migration/carbene insertion/β-H elimination sequence

Ge Zhang; Xiao-Jiao Feng; Meng-Yao Li; Xiao-Ming Ji; Guo-Qiang Lin; Chen-Guo Feng

doi:10.1039/d2ob00751g

Synthesis of tetrasubstituted allenes via a 1,4-palladium migration/carbene insertion/β-H elimination sequence

Org Biomol Chem. 2022 Jul 13;20(27):5383-5386. doi: 10.1039/d2ob00751g.

Authors

Ge Zhang^{1

2}, Xiao-Jiao Feng¹, Meng-Yao Li^{2

3}, Xiao-Ming Ji¹, Guo-Qiang Lin^{1

2}, Chen-Guo Feng^{1

2}

Affiliations

¹ The Research Center of Chiral Drugs, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai, 201203, China. [email protected].
² Key Laboratory of Synthetic Chemistry of Natural Substances, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Shanghai, 200032, China.
³ State Key Laboratory of Oncogenes and Related Genes, Shanghai Cancer Institute, Renji Hospital, Shanghai Jiao Tong University School of Medicine, Shanghai, China.

PMID: 35748786
DOI: 10.1039/d2ob00751g

Abstract

A palladium-catalyzed synthesis of tetrasubstituted allenes from aryl bromides and aryl diazoacetates is developed. This transformation proceeded via an aryl to alkenyl 1,4-palladium migration/carbene insertion/β-H elimination sequence under mild reaction conditions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkadienes*
Catalysis
Methane / analogs & derivatives
Palladium*

Substances

Alkadienes
carbene
propadiene
Palladium
Methane