A Synthetic Route to Sodium α-Aminoalkanesulfinates and Their Application in the Generation of α-Aminoalkyl Radicals for Radical Addition Reactions

被引：14
|
作者：
Sakamoto, Ryu [1 ]
Yoshii, Tomomi [1 ]
Takada, Hiroyuki [1 ]
Maruoka, Keiji [1 ,2 ]
机构：
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
[2] Guangdong Univ Technol, Sch Chem Engn & Light Ind, HEMC, 100 West Waihuan Rd,4 Panyu Dist, Guangzhou 510006, Guangdong, Peoples R China
来源：
ORGANIC LETTERS | 2018年 / 20卷 / 07期
关键词：
LIGHT PHOTOREDOX CATALYSIS; DIOXIDE SURROGATE DABSO; CONJUGATE ADDITIONS; SULFONE SYNTHESIS; SULFUR-DIOXIDE; PHENANTHRIDINE DERIVATIVES; DECARBOXYLATIVE ARYLATION; UNACTIVATED ALKENES; ORGANIC-SYNTHESIS; CROSS-COUPLINGS;
D O I：
10.1021/acs.orglett.8b00621
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of sodium alpha-aminoalkanesulfinates and their synthetic utility as alpha-aminoalkyl radical precursors are reported. A variety of alpha-aminoalkanesulfinates were readily obtained from the reaction between the anions of N-Boc-protected alkylamines and 1,4-diazabicyclo[2.2.2]octanebis(sulfur dioxide). Treatment of sodium alpha-aminoalkanesulfinates with (diacetoxyiodo)benzene easily generated the corresponding alpha-aminoalkyl radicals under mild conditions, which were then applied in radical 1,2-addition to imines, radical 1,4-addition to electron-deficient olefins, and radical addition/cyclization to 2-isocyanobiphenyls.
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页码：2080 / 2083
页数：4
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