TY - JOUR
T1 - Iodo(III)-Meyer−Schuster rearrangement of propargylic alcohols promoted by benziodoxole triflate
AU - Laskar, Roshayed Ali
AU - Ding, Wei
AU - Yoshikai, Naohiko
N1 - Funding Information:
This work was supported by the Singapore Ministry of Education Academic Research Funds Tier 2 (MOE2016-T2-2-043) and Tier 1 (RG114/18) as well as the Agency for Science, Technology and Research (A*STAR) AME IRG grant (A2083c0056). We thank Dr. Yongxin Li (Nanyang Technological University) for his assistance with the X-ray crystallographic analysis.
Publisher Copyright:
© 2021 American Chemical Society
PY - 2021/2/5
Y1 - 2021/2/5
N2 - Benziodoxole triflate (BXT), a cyclic iodine(III) electrophile, has been found to promote a rearrangement of propargylic alcohols into α,β-unsaturated ketones bearing an α-λ3iodanyl group. This iodo(III)-Meyer−Schuster rearrangement proceeds under mild conditions and tolerates a variety of functionalized propargylic alcohols, thus complementing previously reported halogen-intercepted Meyer−Schuster rearrangement. The α-λ3-iodanylenones can be utilized for facile Pd-catalyzed cross-coupling for the synthesis of multisubstituted enones.
AB - Benziodoxole triflate (BXT), a cyclic iodine(III) electrophile, has been found to promote a rearrangement of propargylic alcohols into α,β-unsaturated ketones bearing an α-λ3iodanyl group. This iodo(III)-Meyer−Schuster rearrangement proceeds under mild conditions and tolerates a variety of functionalized propargylic alcohols, thus complementing previously reported halogen-intercepted Meyer−Schuster rearrangement. The α-λ3-iodanylenones can be utilized for facile Pd-catalyzed cross-coupling for the synthesis of multisubstituted enones.
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U2 - 10.1021/acs.orglett.1c00039
DO - 10.1021/acs.orglett.1c00039
M3 - Article
C2 - 33439023
AN - SCOPUS:85099924729
SN - 1523-7060
VL - 23
SP - 1113
EP - 1117
JO - Organic Letters
JF - Organic Letters
IS - 3
ER -