Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (3): 1193-1199.DOI: 10.6023/cjoc202008030 Previous Articles Next Articles
ARTICLES
王琦a, 朱柏燃a, 杨光a, 马献涛a,b,*(), 徐清a,c,*()
收稿日期:
2020-08-17
修回日期:
2020-10-04
发布日期:
2020-10-28
通讯作者:
马献涛, 徐清
基金资助:
Qi Wanga, Boran Zhua, Guang Yanga, Xiantao Maa,b,*(), Qing Xua,c,*()
Received:
2020-08-17
Revised:
2020-10-04
Published:
2020-10-28
Contact:
Xiantao Ma, Qing Xu
About author:
Supported by:
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Qi Wang, Boran Zhu, Guang Yang, Xiantao Ma, Qing Xu. Selective Synthesis of Unsymmetrical N-Heteroaryl Thioethers byBase-Free Direct Multi-Component Reaction[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1193-1199.
Entry | Base (equiv.) | Solvent (mL) | T., t | Yieldb/% |
---|---|---|---|---|
1 | Basesc (2) | None | 140 ℃, 24 h | Trace~35 |
2 | None | None | 140 ℃, 24 h | 33 |
3 | None | None | (i) 80 ℃, 1 h; (ii) 140 ℃, 24 h | 43 (A)d |
4 | None | None | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 59 (A)d |
5 | None | None | (i) 80 ℃, 1 h; (i) 170 ℃, 24 h | 69 (A)d,e |
6 | None | CH3CN (1) | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 21 (A)d,e |
7 | None | EtOH (1) | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 10 (A)d,e |
8 | None | None | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 61 (B)e,f |
Entry | Base (equiv.) | Solvent (mL) | T., t | Yieldb/% |
---|---|---|---|---|
1 | Basesc (2) | None | 140 ℃, 24 h | Trace~35 |
2 | None | None | 140 ℃, 24 h | 33 |
3 | None | None | (i) 80 ℃, 1 h; (ii) 140 ℃, 24 h | 43 (A)d |
4 | None | None | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 59 (A)d |
5 | None | None | (i) 80 ℃, 1 h; (i) 170 ℃, 24 h | 69 (A)d,e |
6 | None | CH3CN (1) | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 21 (A)d,e |
7 | None | EtOH (1) | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 10 (A)d,e |
8 | None | None | (i) 80 ℃, 1 h; (ii) 170 ℃, 24 h | 61 (B)e,f |
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In our previous work, it has been observed that the contaminant water in the substrates and the reaction vessel (Ref. [10a]) and even the crystal water (Ref. [10b]) can facilitate the sulfur transfer reactions. As having been discussed (Ref. [10] and references cited therein), water plays a key role in the reaction mechanism by hydrolyzing the in situ generated ionic intermediates (such as 4 and 6 in this work, Scheme 3) to the corresponding thiols. However, in this work, addition of water to the reactions of other alkyl halides mostly led to reduce the yields of products. This may be due to the easy hydrolysis of the alkyl halides in the presence of water. This may also mean that, in this work, the contaminant water in the substrates and the reaction vessel is adequate to facilitate the reactions and thus no additional water is needed.
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