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.

引用

页码：2080 / 2083

页数：4

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