TY - JOUR
T1 - Regio- and Diastereoselective Vicinal Aminobromination of Electron Deficient Olefins via Phosphorus-Based GAP Protocol
AU - Rahman, Anis Ur
AU - Zarshad, Nighat
AU - Khan, Iltaf
AU - Faiz, Faisal
AU - Li, Guigen
AU - Ali, Asad
N1 - Funding Information:
We would like to acknowledge the financial support from the National Natural Science Foundation of China (No. 22071102 and 91956110) and Robert A. Welch Foundation (D-1361, United States).
Publisher Copyright:
© Copyright © 2021 Rahman, Zarshad, Khan, Faiz, Li and Ali.
PY - 2021/9/8
Y1 - 2021/9/8
N2 - Chemical synthesis based on Group-Assisted Purification chemistry (GAP) has been prolifically used as a powerful, greener and ecofriendly tool so far. Herein, we report hypervalent iodine (III) mediated regio- and diastereoselective aminobromination of electron-deficient olefins using group-assisted purification (GAP) method. By simply mixing the GAP auxiliary-anchored substrates with TsNH2–NBS as nitrogen/bromine sources and PhI(OAc)2 as a catalyst, a series of vicinal bromoamines with multifunctionalities were obtained in moderate to excellent yields (53–94%). The vicinal bromoamines were obtained without column chromatography and/or recrystallization simply by washing the crude mixtures with cosolvents and thus avoiding wastage of silica, solvents, time, and labor. The GAP auxiliary is recyclable and reusable.
AB - Chemical synthesis based on Group-Assisted Purification chemistry (GAP) has been prolifically used as a powerful, greener and ecofriendly tool so far. Herein, we report hypervalent iodine (III) mediated regio- and diastereoselective aminobromination of electron-deficient olefins using group-assisted purification (GAP) method. By simply mixing the GAP auxiliary-anchored substrates with TsNH2–NBS as nitrogen/bromine sources and PhI(OAc)2 as a catalyst, a series of vicinal bromoamines with multifunctionalities were obtained in moderate to excellent yields (53–94%). The vicinal bromoamines were obtained without column chromatography and/or recrystallization simply by washing the crude mixtures with cosolvents and thus avoiding wastage of silica, solvents, time, and labor. The GAP auxiliary is recyclable and reusable.
KW - aziridinium
KW - diastereoselectivity
KW - iodobenzene diacetate
KW - nitrogen/halogen source
KW - protecting groups
UR - http://www.scopus.com/inward/record.url?scp=85115408771&partnerID=8YFLogxK
U2 - 10.3389/fchem.2021.742399
DO - 10.3389/fchem.2021.742399
M3 - Article
AN - SCOPUS:85115408771
SN - 2296-2646
VL - 9
JO - Frontiers in Chemistry
JF - Frontiers in Chemistry
M1 - 742399
ER -