Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups | Zendy

Eric Tan | Zendy; Ophélie Quiro | Zendy; M. Elena de Orbe | Zendy; Antonio M. Echavarren | Zendy

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Broad-Scope Rh-Catalyzed Inverse-Sonogashira Reaction Directed by Weakly Coordinating Groups

Author(s) -

Eric Tan,

Ophélie Quiro,

M. Elena de Orbe,

Antonio M. Echavarren

Publication year - 2018

Publication title -

acs catalysis

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 4.898

H-Index - 198

ISSN - 2155-5435

DOI - 10.1021/acscatal.7b04395

Subject(s) - sonogashira coupling , catalysis , scope (computer science) , chemistry , rhodium , combinatorial chemistry , inverse , palladium , organic chemistry , computer science , mathematics , geometry , programming language

We report the alkynylation of C(sp 2 )-H bonds with bromoalkynes (inverse-Sonogashira reaction) directed by synthetically useful ester, ketone, and ether groups under rhodium catalysis. Other less common directing groups such as amine, thioether, sulfoxide, sulfone, phenol ester, and carbamate are also suitable directing groups. Mechanistic studies indicate that the reaction proceeds by a turnover-limiting C-H activation step via an electrophilic-type substitution.

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