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Upgrading CO 2 by Incorporation into Urethanes through Silver‐Catalyzed One‐Pot Stepwise Amidation Reaction
Author(s) -
Song QingWen,
Liu Ping,
Han LiHua,
Zhang Kan,
He LiangNian
Publication year - 2018
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201700572
Subject(s) - chemistry , catalysis , turnover number , selectivity , reaction conditions , carbon dioxide , organic chemistry , nuclear chemistry
One‐pot two‐step stepwise reaction of terminal propargylic alcohols, carbon dioxide, and primary/secondary amines for the effective synthesis of various urethanes through robust silver‐catalysed C‐O/C‐N bond formation is reported. Catalytic activities were investigated by controlling catalyst loading, reaction pressure and time, and very high turnover number (turnover frequency) was obtained: 3350 (35 h −1 ) with 0.01 mol% silver catalyst under 0.1 MPa, and up to 13360 (139 h −1 ) with 0.005 mol% silver catalyst under 2.0 MPa at room temperature. The strategy was ingeniously regulated, and synchronously afforded a wide range of β‐oxopropylcarbamate and 1,3‐oxazolidin‐2‐one motifs in excellent yields and selectivity together with unprecedented high turnover number (TON) and turnover frequency (TOF) value.