Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 38, Pages 11906-11910Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b07418
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Funding
- Dreyfus Foundation
- Agency of Science, Technology and Research (A*STaR), Singapore
- Caltech's SURF program
- Caltech's WAVE program
- NSF [CRIF:MU CHE0639094]
- NIH [RR027690]
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We report the synthesis and reactivity of Zr complexes supported by a 9,10-anthracenediyl-linked bisphenoxide ligand, L. (ZrLBn2)-L-IV (1) undergoes facile photolytic reduction with concomitant formation of bibenzyl and (ZrL)-L-IV(THF)(3) (2), which displays a two electron reduced anthracene moiety. Leveraging ligand-stored reducing equivalents, 2 promotes the oxidative coupling of internal and terminal alkynes to isolable zirconacyclopentadiene complexes, demonstrating the reversible utilization of anthracene as a redox reservoir. With diphenylacetylene under CO, cyclopentadienone is formed stoichiometrically. 2 is competent for the catalytic formation of pyrimidines from alkynes and nitriles. Mechanistic studies suggest that selectivity for pyrimidine originates from preferred formation of an azazirconacyclopentadiene intermediate, which reacts preferentially with nitriles over alkynes.
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