4.6 Article

Zinc-Catalysed Hydroboration of Terminal and Internal Alkynes

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 14, Issue 24, Pages 4553-4556

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201900839

Keywords

boronate ester; chemoselective; homogeneous catalysis; hydroboration; zinc

Funding

  1. SERB [EMR/2016/000367]
  2. Indian Institute of Science (IISc) start-up research grant
  3. Kishore Vaigyanik Protsahan Yojana (KVPY)
  4. DST inspire faculty award [DST/INSPIRE/04/2015/000785]

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A regioselective hydroboration of alkynes has been developed by using commercially available zinc triflate as a catalyst, in the presence of catalytic amount of NaBHEt3. The reaction tolerates a wide range of terminal alkynes having several synthetically useful functional groups and proceeds regioselectively to furnish hydroborated products in moderate to excellent yields. This system shows moderate chemoselectivity towards terminal C equivalent to C bond over terminal and internal C=C bond and internal C equivalent to C bond.

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