Abstract
The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by σ-bond metathesis.
| Original language | English |
|---|---|
| Pages (from-to) | 12154-12160 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 78 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 2013 Dec 6 |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
Protodeboronation of ortho- and para-phenol boronic acids and application to ortho and meta functionalization of phenols using boronic acids as blocking and directing groups. / Lee, Chun Young; Ahn, Su Jin; Cheon, Cheol-Hong.
In: Journal of Organic Chemistry, Vol. 78, No. 23, 06.12.2013, p. 12154-12160.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Protodeboronation of ortho- and para-phenol boronic acids and application to ortho and meta functionalization of phenols using boronic acids as blocking and directing groups
AU - Lee, Chun Young
AU - Ahn, Su Jin
AU - Cheon, Cheol-Hong
PY - 2013/12/6
Y1 - 2013/12/6
N2 - The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by σ-bond metathesis.
AB - The first metal-free thermal protodeboronation of ortho- and para-phenol boronic acids in DMSO was developed. The protodeboronation was successfully applied to the synthesis of ortho- and meta-functionalized phenols using the boronic acid moiety as a blocking group and a directing group, respectively. Mechanistic studies suggested that this protodeboronation proceeds through the coordination of water to the boron atom followed by σ-bond metathesis.
UR - http://www.scopus.com/inward/record.url?scp=84890186453&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84890186453&partnerID=8YFLogxK
U2 - 10.1021/jo402174v
DO - 10.1021/jo402174v
M3 - Article
C2 - 24187996
AN - SCOPUS:84890186453
VL - 78
SP - 12154
EP - 12160
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -