Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether.

Chem Commun (Camb)

MPC Division, CSIR-Central Drug Research Institute, Jankipuram extension, Sitapur Road, Lucknow 226031, India. and Academy of Scientific and Innovative Research, New Delhi 110001, India and MCB Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.

Published: March 2017

Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.

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http://dx.doi.org/10.1039/c6cc10256eDOI Listing

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