2017
DOI: 10.1021/acs.orglett.7b02125
|View full text |Cite
|
Sign up to set email alerts
|

Chemodivergent, Tunable, and Selective Iodine(III)-Mediated Bromo-Functionalizations of Polyprenoids

Abstract: Mild oxidation of bromides by iodine(III) reagents generated active electrophilic bromination species that were reacted with polyprenoids. By simple and minor variations of an I(III)/Br combination, the reactivity could be selectively steered toward dibromination, oxybromination, or bromocyclization, giving access to a wide array of brominated motifs.

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
3
2

Citation Types

0
13
0

Year Published

2018
2018
2024
2024

Publication Types

Select...
4
1
1

Relationship

2
4

Authors

Journals

citations
Cited by 13 publications
(13 citation statements)
references
References 46 publications
(19 reference statements)
0
13
0
Order By: Relevance
“…In our study on terpenoids [16], the reaction conditions for the dibromination of the distal double bond were easily established from our previous study on the bromination of enamides [11]. Thus, using a slight excess of DIB along with a two-fold amount of lithium bromide at 0 °C in dry acetonitrile rapidly yielded dibromo adduct 2a in 91% yield (Table 1, entry 1).…”
Section: Resultsmentioning
confidence: 99%
See 4 more Smart Citations
“…In our study on terpenoids [16], the reaction conditions for the dibromination of the distal double bond were easily established from our previous study on the bromination of enamides [11]. Thus, using a slight excess of DIB along with a two-fold amount of lithium bromide at 0 °C in dry acetonitrile rapidly yielded dibromo adduct 2a in 91% yield (Table 1, entry 1).…”
Section: Resultsmentioning
confidence: 99%
“…Despite the potential sensitivity of the alcohol and the amine functions, both geraniol ( 1c ) and protected geranylamine 1d gave the dibromo adduct 2c [16] and 2d in good yields. Finally, the reaction was performed on myrcene ( 1e ), providing 2e in 78% yield and leaving the diene moiety untouched.…”
Section: Resultsmentioning
confidence: 99%
See 3 more Smart Citations