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Sequential functionalization of alkynes and alkenes catalyzed by gold(I) and palladium(II) N-heterocyclic carbene complexes

(2016) CHEMCATCHEM. 8(21). p.3381-3388
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Organization
Abstract
The iodination of terminal alkynes for the synthesis of 1-iodoalkynes using N-iodosuccinimide in the presence of a Au-I-NHC (NHC=N-heterocyclic carbene) catalyst is reported. A series of aromatic alkynes was transformed successfully into the corresponding 1-iodoalkynes in good to excellent yields under mild reaction conditions. The further use of these compounds as organic building blocks and the advantageous choice of metal-NHC complexes as catalysts for alkyne functionalization were further demonstrated by performing selective Au-I-catalyzed hydrofluorination to yield (Z)-2-fluoro-1-iodoalkenes, followed by a Suzuki-Miyaura cross-coupling with aryl boronic acids catalyzed by a Pd-II-NHC complex to access trisubstituted (Z)-fluoroalkenes. All methodologies can be performed sequentially with only minor variations in the optimized individual reaction conditions, maintaining high efficiency and selectivity in all cases, which therefore, provides straightforward access to valuable fluorinated alkenes from commercially available terminal alkynes.
Keywords
alkynes, cross-coupling, gold, carbenes, palladium, ONE-POT SYNTHESIS, CROSS-COUPLING REACTIONS, TERMINAL ALKYNES, STEREOSELECTIVE-SYNTHESIS, REGIOSELECTIVE SYNTHESIS, SUZUKI-MIYAURA, CYCLOADDITION REACTIONS, HOMOCOUPLING REACTION, DIRECT IODINATION, ORGANIC-SYNTHESIS

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Citation

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MLA
Gomez-Herrera, Alberto et al. “Sequential Functionalization of Alkynes and Alkenes Catalyzed by gold(I) and palladium(II) N-heterocyclic Carbene Complexes.” CHEMCATCHEM 8.21 (2016): 3381–3388. Print.
APA
Gomez-Herrera, A., Nahra, F., Brill, M., Nolan, S., & Cazin, C. (2016). Sequential functionalization of alkynes and alkenes catalyzed by gold(I) and palladium(II) N-heterocyclic carbene complexes. CHEMCATCHEM, 8(21), 3381–3388.
Chicago author-date
Gomez-Herrera, Alberto, Fady Nahra, Marcel Brill, Steven Nolan, and Catherine Cazin. 2016. “Sequential Functionalization of Alkynes and Alkenes Catalyzed by gold(I) and palladium(II) N-heterocyclic Carbene Complexes.” Chemcatchem 8 (21): 3381–3388.
Chicago author-date (all authors)
Gomez-Herrera, Alberto, Fady Nahra, Marcel Brill, Steven Nolan, and Catherine Cazin. 2016. “Sequential Functionalization of Alkynes and Alkenes Catalyzed by gold(I) and palladium(II) N-heterocyclic Carbene Complexes.” Chemcatchem 8 (21): 3381–3388.
Vancouver
1.
Gomez-Herrera A, Nahra F, Brill M, Nolan S, Cazin C. Sequential functionalization of alkynes and alkenes catalyzed by gold(I) and palladium(II) N-heterocyclic carbene complexes. CHEMCATCHEM. 2016;8(21):3381–8.
IEEE
[1]
A. Gomez-Herrera, F. Nahra, M. Brill, S. Nolan, and C. Cazin, “Sequential functionalization of alkynes and alkenes catalyzed by gold(I) and palladium(II) N-heterocyclic carbene complexes,” CHEMCATCHEM, vol. 8, no. 21, pp. 3381–3388, 2016.
@article{8536967,
  abstract     = {The iodination of terminal alkynes for the synthesis of 1-iodoalkynes using N-iodosuccinimide in the presence of a Au-I-NHC (NHC=N-heterocyclic carbene) catalyst is reported. A series of aromatic alkynes was transformed successfully into the corresponding 1-iodoalkynes in good to excellent yields under mild reaction conditions. The further use of these compounds as organic building blocks and the advantageous choice of metal-NHC complexes as catalysts for alkyne functionalization were further demonstrated by performing selective Au-I-catalyzed hydrofluorination to yield (Z)-2-fluoro-1-iodoalkenes, followed by a Suzuki-Miyaura cross-coupling with aryl boronic acids catalyzed by a Pd-II-NHC complex to access trisubstituted (Z)-fluoroalkenes. All methodologies can be performed sequentially with only minor variations in the optimized individual reaction conditions, maintaining high efficiency and selectivity in all cases, which therefore, provides straightforward access to valuable fluorinated alkenes from commercially available terminal alkynes.},
  author       = {Gomez-Herrera, Alberto and Nahra, Fady and Brill, Marcel and Nolan, Steven and Cazin, Catherine},
  issn         = {1867-3880},
  journal      = {CHEMCATCHEM},
  keywords     = {alkynes,cross-coupling,gold,carbenes,palladium,ONE-POT SYNTHESIS,CROSS-COUPLING REACTIONS,TERMINAL ALKYNES,STEREOSELECTIVE-SYNTHESIS,REGIOSELECTIVE SYNTHESIS,SUZUKI-MIYAURA,CYCLOADDITION REACTIONS,HOMOCOUPLING REACTION,DIRECT IODINATION,ORGANIC-SYNTHESIS},
  language     = {eng},
  number       = {21},
  pages        = {3381--3388},
  title        = {Sequential functionalization of alkynes and alkenes catalyzed by gold(I) and palladium(II) N-heterocyclic carbene complexes},
  url          = {http://dx.doi.org/10.1002/cctc.201600868},
  volume       = {8},
  year         = {2016},
}

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