Open Access
Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates
Publication type: Journal Article
Publication date: 2018-11-15
scimago Q1
wos Q1
SJR: 10.416
CiteScore: 48.4
Impact factor: 45.8
ISSN: 00368075, 10959203
PubMed ID:
30442804
Multidisciplinary
Abstract
Heterocycles meet and marry on phosphorus
Metals such as palladium are routinely used to link together carbon rings in pharmaceutical synthesis. However, the presence of nitrogen in both rings can trip up this process. Hilton et al. report a versatile alternative process in which phosphorus takes the place of the metal. The phosphorus binds successively to both rings at the sites opposite the nitrogen, and treatment with acidic ethanol then pushes them off, bound to each other. Theory implicates a five-coordinate phosphorus intermediate that kinetically favors coupling of the two nitrogen-bearing rings over reactions of the other all-carbon substituents.
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Metrics
194
Total citations:
194
Citations from 2024:
64
(33.16%)
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GOST
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Hilton M. C. et al. Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates // Science. 2018. Vol. 362. No. 6416. pp. 799-804.
GOST all authors (up to 50)
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Hilton M. C., Zhang X., Boyle D. T., Alegre‐Requena J. V., Paton R. F., McNally A. Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates // Science. 2018. Vol. 362. No. 6416. pp. 799-804.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1126/science.aas8961
UR - https://doi.org/10.1126/science.aas8961
TI - Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates
T2 - Science
AU - Hilton, Michael C
AU - Zhang, Xuan
AU - Boyle, David T
AU - Alegre‐Requena, Juan V.
AU - Paton, Robert F.
AU - McNally, Andrew
PY - 2018
DA - 2018/11/15
PB - American Association for the Advancement of Science (AAAS)
SP - 799-804
IS - 6416
VL - 362
PMID - 30442804
SN - 0036-8075
SN - 1095-9203
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2018_Hilton,
author = {Michael C Hilton and Xuan Zhang and David T Boyle and Juan V. Alegre‐Requena and Robert F. Paton and Andrew McNally},
title = {Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates},
journal = {Science},
year = {2018},
volume = {362},
publisher = {American Association for the Advancement of Science (AAAS)},
month = {nov},
url = {https://doi.org/10.1126/science.aas8961},
number = {6416},
pages = {799--804},
doi = {10.1126/science.aas8961}
}
Cite this
MLA
Copy
Hilton, Michael C., et al. “Heterobiaryl synthesis by contractive C–C coupling via P(V) intermediates.” Science, vol. 362, no. 6416, Nov. 2018, pp. 799-804. https://doi.org/10.1126/science.aas8961.