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Ru(II)‐Catalyzed Regioselective Hydroarylative Coupling of Indolines with Internal Alkynes by C−H Activation
Author(s) -
Kumar Mohit,
Khan Afsar Ali,
Dutta Himangsu Sekhar,
Ahmad Ashfaq,
Vaishnav Jayanti,
Kant Ruchir,
Ampapathi Ravi Sankar,
Koley Dipankar
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100085
Subject(s) - regioselectivity , chemistry , electrophile , catalysis , alkyne , combinatorial chemistry , atom economy , molecule , stereochemistry , organic chemistry
We have developed a regioselective hydroarylative coupling of indolines with internal alkynes by the activation of C−H bond using inexpensive Ru(II)‐catalyst. This redox‐neutral, atom‐economical, and scalable C−H functionalization has been accomplished using easily removable weakly coordinating directing group. Diverse unsymmetrically substituted alkynes appended with pharmacologically important heterocycles were coupled with various indolines and 1,2,3,4‐tetrahydroquinolines to furnish the corresponding trisubstituted alkenes with very high regioselectivity. The application of the method has been demonstrated with a number of alkyne‐containing drug molecules, natural products, carbohydrates, amino acids, steroids, and other heterocycles. Preliminary mechanistic interrogation revealed that the C−H activation proceeds through base‐assisted internal electrophilic‐type substitution process.