(CAAC)CuX-catalyzed hydroboration of terminal alkynes with pinacolborane directed by the X-ligand

Romero, Erik A.; Jazzar, Rodolphe; Bertrand, Guy

doi:10.1016/j.jorganchem.2016.09.025

(CAAC)CuX-catalyzed hydroboration of terminal alkynes with pinacolborane directed by the X-ligand

Journal Article · Wed Sep 28 00:00:00 EDT 2016 · Journal of Organometallic Chemistry

DOI:https://doi.org/10.1016/j.jorganchem.2016.09.025· OSTI ID:1534026

Romero, Erik A. ^[1]; Jazzar, Rodolphe ^[2]; Bertrand, Guy ^[2]

University of California, San Diego, CA (United States); DOE/OSTI
University of California, San Diego, CA (United States)

We report when X is a basic ligand (CAAC)CuX complexes [CAAC = cyclic (alkyl) (amino)carbene] selectively promote the (E)-β-hydroboration of terminal alkynes with pinacolborane instead of the dehydrogenative borylation observed with weakly nucleophilic X ligand. This methodology is applicable to a variety of terminal alkynes. Deuterium labeling experiments coupled with stoichiometric reactions give evidence towards a plausible mechanism involving a σ-mono (copper)acetylide complex.

View Accepted Manuscript (DOE)

Research Organization:: University of California, San Diego, CA (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: SC0009376

OSTI ID:: 1534026

Alternate ID(s):: OSTI ID: 1397758

Journal Information:: Journal of Organometallic Chemistry, Journal Name: Journal of Organometallic Chemistry Journal Issue: C Vol. 829; ISSN 0022-328X

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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