Uploaded May 2022 | Updated September 2026, 1 week ago

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In this episode, I discuss 1,2-shifts of boron-containing motifs, including hydroboration/oxidation, the Matteson reaction, Zweifel olefination, and Aggarwal rearrangement.

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Links to articles discussed in this episode:

For the CDI/NaN3 example, here is a reference that accomplishes the transformation:
doi.org/10.1021/jo00285a022

hydroboration - doi.org/10.1021/ja01510a059
1st boron oxidation - doi.org/10.1002/anie.200460178
2nd boron oxidation - doi.org/10.1021/op2002497
1st phenol - doi.org/10.1002/bkcs.12012
2nd phenol - doi.org/10.1016/j.tetlet.2017.10.047
Matteson reaction - doi.org/10.1021/ja00900a017
1st Matteson example - doi.org/10.1021/ja00545a045
2nd Matteson example - doi.org/10.1016/S0022-328X(00)00595-7
Silyl-Matteson - doi.org/10.1021/om00074a006
cis-alkene Zweifel - doi.org/10.1021/ja00990a061
trans-alkene Zweifel - doi.org/10.1021/ja00773a059
Aggarwal homologation - doi.org/10.1021/ja043632k
Aggarwal example - doi.org/10.1002/anie.201907617
Evans paper - doi.org/10.1021/ja00257a041
tertiary review - doi.org
Aggarwal group website - chm.bris.ac.uk/org/aggarwal/publications.php
alkyl shift review - doi.org/10.1351/pac200678020215
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