Synlett 2024; 35(11): 1259-1264
DOI: 10.1055/a-2170-2976
cluster
Japan/Netherlands Gratama Workshop

Reaction of Highly Volatile Organic Compounds with Organolithium Species in Flow Microreactor

Kensuke Muta
a   Fundamental Chemical Research Center, Central Glass Co., Ltd., 17-5, Nakadai 2-chome, Kawagoe City, Saitama 350-1159, Japan
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b   Department of Chemistry, Graduate School of Science, Hokkaido University, Kita 10-jo, Nishi 8-chome, Kita-ku, Sapporo 060-0810, Japan
,
b   Department of Chemistry, Graduate School of Science, Hokkaido University, Kita 10-jo, Nishi 8-chome, Kita-ku, Sapporo 060-0810, Japan
› Author Affiliations
This work was supported by Japan Society for the Promotion of Science (JSPS KAKENHI) Grant Numbers, JP23K04744 (Grant-in-Aid for Scientific Research (C)), JP20KK0121 (Fostering Joint International Research (B)), JP21H01936 (Grant-in-Aid for Scientific Research (B)), JP21H01706 (Grant-in-Aid for Scientific Research (B)), and JP21H05080 (Grant-in-Aid for Transformative Research Areas (B)). This work was also partially supported by the Japan Agency for Medical Research and Development (AMED, JP21ak0101156), the Core Research for Evolutional Science and Technology (CREST, JPMJCR18R1), the New Energy and Industrial Technology Development Organization (NEDO, PJ22031410 and PJ22220030), the Japan Keirin Autorace Foundation (JKA Foundation), the Ogasawara Foundation for the Promotion of Science and Engineering, and the Takahashi Industrial and Economic Foundation.


Abstract

Highly volatile organic compounds (VOCs) with boiling points (bp) around or below room temperature are generally difficult to manipulate precisely in liquid-phase organic reactions although they offer significant atom-economic advantages. We have developed a novel approach using a jacketed syringe pump to enable the formylation of organolithium species in a continuous-flow system under ambient pressure. Methyl formate (bp 32 °C) worked as a formylating agent and was successfully delivered to the continuous operation for over 30 minutes in our microflow system. This methodology was successfully expanded to the application of acetaldehyde (bp 21 °C) and heptafluoropropyl bromide (bp 12 °C).

Supporting Information



Publication History

Received: 06 August 2023

Accepted after revision: 07 September 2023

Accepted Manuscript online:
07 September 2023

Article published online:
30 October 2023

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