4.8 Article

Formation of C(sp2)-Boronate Esters by Borylative Cyclization of Alkynes Using BCl3

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 54, Issue 38, Pages 11245-11249

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201505810

Keywords

alkynes; boron; cyclizations; heterocycles; synthetic methods

Funding

  1. European Research Council (FP7) [305868]
  2. EPSRC [EP/J000973/1, EP/ K039547/1]
  3. Royal Society
  4. Engineering and Physical Sciences Research Council [EP/K039547/1, EP/J000973/1, 1537618] Funding Source: researchfish
  5. EPSRC [EP/J000973/1, EP/K039547/1] Funding Source: UKRI

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BCl3 is an inexpensive electrophile which induces the borylative cyclization of a wide range of substituted alkynes to regioselectively form polycycles containing synthetically versatile C(sp(2))-boronate esters. It proceeds rapidly, with good yields and is compatible with a range of functional groups and substitution patterns. Intermolecular 1,2-carboboration of alkynes is also achieved using BCl3 to generate trisubstituted vinyl boronate esters.

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