Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether.
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.
MPC Division, CSIR-Central Drug Research Institute, Jankipuram extension, Sitapur Road, Lucknow 226031, India. msreddy@cdri.res.in.
Madala
M
Hari Babu
MPC Division, CSIR-Central Drug Research Institute, Jankipuram extension, Sitapur Road, Lucknow 226031, India. msreddy@cdri.res.in and Academy of Scientific and Innovative Research, New Delhi 110001, India.
Gadi
G
Ranjith Kumar
MSB Division, CSIR-Central Drug Research Institute, Jankipuram extension, Sitapur Road, Lucknow 226031, India.
Ruchir
R
Kant
MPC Division, CSIR-Central Drug Research Institute, Jankipuram extension, Sitapur Road, Lucknow 226031, India. msreddy@cdri.res.in and Academy of Scientific and Innovative Research, New Delhi 110001, India and MCB Division, CSIR-Indian Institute of Chemical Technology, Hyderabad, India.
Maddi
http://orcid.org/0000-0003-4961-8314
M
Sridhar Reddy