para-Selective Arylation of Arenes: A Direct Route to Biaryls by Norbornene Relay Palladation
Dr. Uttam Dutta
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
These authors contributed equally to this work.
Search for more papers by this authorSandip Porey
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
These authors contributed equally to this work.
Search for more papers by this authorSandeep Pimparkar
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorAstam Mandal
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorJagrit Grover
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorAdithyaraj Koodan
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorCorresponding Author
Dr. Debabrata Maiti
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Tokyo Tech World Research Hub Initiative (WRHI) Laboratory for Chemistry and Life Science, Tokyo Institute of Technology, Tokyo, 152-8550 Japan
Search for more papers by this authorDr. Uttam Dutta
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
These authors contributed equally to this work.
Search for more papers by this authorSandip Porey
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
These authors contributed equally to this work.
Search for more papers by this authorSandeep Pimparkar
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorAstam Mandal
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorJagrit Grover
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorAdithyaraj Koodan
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Search for more papers by this authorCorresponding Author
Dr. Debabrata Maiti
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400 076 India
Tokyo Tech World Research Hub Initiative (WRHI) Laboratory for Chemistry and Life Science, Tokyo Institute of Technology, Tokyo, 152-8550 Japan
Search for more papers by this authorDedicated to Professor Sourav Pal on the occasion of his 65th birthday
Abstract
Biaryl compounds are extremely important structural motifs in natural products, biologically active components and pharmaceuticals. Selective synthesis of biaryls by distinguishing the subtle reactivity difference of distal arene C−H bonds are significantly challenging. Herein, we describe para-selective C−H arylation, which is acheived by a unique combination of a meta-directing group and norbornene as a transient mediator. Upon direct meta-C−H palladation, one-bond relay palladation occurs in presence of norbornene and subsequently para-C−H arylation is achieved for sulfonates, phosphonates and phenols bearing 2,6-disubstitution patterns. The protocol is amenable to electron-deficient aryl iodides. Multisubstituted arenes and phenols are obtained by postsynthetic modification of the products. The protocol allows the synthesis of hexa-substituted benzene by sequential selective distal C−H functionalization.
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