Chemical Reviews, volume 119, issue 13, pages 8192-8228
Cross-Coupling of Heteroatomic Electrophiles.
1
Department of Chemistry and Biochemistry, University of Delaware Newark, Delaware 19716, United States
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Publication type: Journal Article
Publication date: 2019-06-11
Journal:
Chemical Reviews
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 62.1
ISSN: 00092665, 15206890
PubMed ID:
31184483
General Chemistry
Abstract
At the advent of cross-coupling chemistry, carbon electrophiles based on halides or pseudohalides were the only suitable electrophilic coupling partners. Almost two decades passed before the first cross-coupling reaction of heteroatom-based electrophiles was reported. Early work by Murai and Tanaka initiated investigations into silicon electrophiles. Narasaka and Johnson pioneered the way in the use of nitrogen electrophiles, while Suginome began the exploration of boron electrophiles. The chemistry reviewed within provides perspective on the use of heteroatomic electrophiles, specifically silicon-, nitrogen-, boron-, oxygen-, and phosphorus-based electrophiles in transition-metal catalyzed cross-coupling. For the purposes of this review, a loose definition of cross-coupling is utilized; all reactions minimally proceed via an oxidative addition event. Although not cross-coupling in a traditional sense, we have also included catalyzed reactions that join a heteroatomic electrophile with an in situ generated nucleophile. However, for brevity, those involving hydroamination or C-H activation as a key step are largely excluded. This work includes primary references published up to and including October 2018.
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- Statistics recalculated weekly.
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Korch K. M., WATSON D. P. Cross-Coupling of Heteroatomic Electrophiles. // Chemical Reviews. 2019. Vol. 119. No. 13. pp. 8192-8228.
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Korch K. M., WATSON D. P. Cross-Coupling of Heteroatomic Electrophiles. // Chemical Reviews. 2019. Vol. 119. No. 13. pp. 8192-8228.
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TY - JOUR
DO - 10.1021/acs.chemrev.8b00628
UR - https://doi.org/10.1021/acs.chemrev.8b00628
TI - Cross-Coupling of Heteroatomic Electrophiles.
T2 - Chemical Reviews
AU - Korch, Katerina M
AU - WATSON, DONALD P.
PY - 2019
DA - 2019/06/11 00:00:00
PB - American Chemical Society (ACS)
SP - 8192-8228
IS - 13
VL - 119
PMID - 31184483
SN - 0009-2665
SN - 1520-6890
ER -
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@article{2019_Korch,
author = {Katerina M Korch and DONALD P. WATSON},
title = {Cross-Coupling of Heteroatomic Electrophiles.},
journal = {Chemical Reviews},
year = {2019},
volume = {119},
publisher = {American Chemical Society (ACS)},
month = {jun},
url = {https://doi.org/10.1021/acs.chemrev.8b00628},
number = {13},
pages = {8192--8228},
doi = {10.1021/acs.chemrev.8b00628}
}
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Korch, Katerina M., and DONALD P. WATSON. “Cross-Coupling of Heteroatomic Electrophiles..” Chemical Reviews, vol. 119, no. 13, Jun. 2019, pp. 8192-8228. https://doi.org/10.1021/acs.chemrev.8b00628.