Title |
Tridentate Directing Groups Stabilize 6‑Membered Palladacycles in Catalytic Alkene Hydrofunctionalization
|
---|---|
Published in |
Journal of the American Chemical Society, October 2017
|
DOI | 10.1021/jacs.7b08383 |
Pubmed ID | |
Authors |
Miriam L. O’Duill, Rei Matsuura, Yanyan Wang, Joshua L. Turnbull, John A. Gurak, De-Wei Gao, Gang Lu, Peng Liu, Keary M. Engle |
Abstract |
Removable tridentate directing groups inspired by pincer ligands have been designed to stabilize otherwise kinetically and thermodynamically disfavored 6-membered alkyl palladacycle intermediates. This family of directing groups enables regioselective remote hydrocarbofunctionalization of several synthetically useful alkene-containing substrate classes, including 4-pentenoic acids, allylic alcohols, homoallyl amines, and bis-homoallylamines, under Pd(II) catalysis. In conjunction with previous findings, we demonstrate regiodivergent hydrofunctionalization of 3-butenoic acid derivatives to afford either Markovnikov or anti-Markovnikov addition products depending on directing group choice. Preliminary mechanistic and computational data are presented to support the proposed catalytic cycle. |
X Demographics
Geographical breakdown
Country | Count | As % |
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United States | 4 | 100% |
Demographic breakdown
Type | Count | As % |
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Scientists | 2 | 50% |
Members of the public | 1 | 25% |
Science communicators (journalists, bloggers, editors) | 1 | 25% |
Mendeley readers
Geographical breakdown
Country | Count | As % |
---|---|---|
Unknown | 83 | 100% |
Demographic breakdown
Readers by professional status | Count | As % |
---|---|---|
Student > Ph. D. Student | 27 | 33% |
Student > Master | 13 | 16% |
Researcher | 9 | 11% |
Student > Bachelor | 5 | 6% |
Student > Doctoral Student | 5 | 6% |
Other | 8 | 10% |
Unknown | 16 | 19% |
Readers by discipline | Count | As % |
---|---|---|
Chemistry | 58 | 70% |
Agricultural and Biological Sciences | 3 | 4% |
Psychology | 1 | 1% |
Biochemistry, Genetics and Molecular Biology | 1 | 1% |
Physics and Astronomy | 1 | 1% |
Other | 1 | 1% |
Unknown | 18 | 22% |