Metal-Free Sulfonylative Spirocyclization of Indolyl-ynones via Insertion of Sulfur Dioxide: Access to Sulfonated Spiro[cyclopentenone-1,3′-indoles]

A metal-free route to alkynyl sulfones under photoinduced conditions is accomplished, starting from 4-alkyl Hantzsch esters, sulfur dioxide, and alkynyl bromides under visible light irradiation at room temperature.

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Transition‐Metal‐Free C2‐H Sulfonylation of Quinoline N ‐Oxides via Insertion of Sulfur Dioxide

Asian Journal of Organic Chemistry ◽

10.1002/ajoc.201900548 ◽

2019 ◽

Vol 8 (11) ◽

pp. 2105-2108 ◽

Cited By ~ 2

Author(s):

Heng Cai ◽

Huiyong Yang ◽

Jun Xu ◽

Hanyang Bao ◽

Lin Huang ◽

...

Keyword(s):

Sulfur Dioxide ◽

Transition Metal ◽

Metal Free

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A four-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, 1,2-dibromoethane, and hydrazines

Organic & Biomolecular Chemistry ◽

10.1039/c5ob01765c ◽

2015 ◽

Vol 13 (41) ◽

pp. 10370-10375 ◽

Cited By ~ 23

Author(s):

Danqing Zheng ◽

Yunyan Kuang ◽

Jie Wu

Keyword(s):

Sulfur Dioxide ◽

Functional Group ◽

Metal Free

A four-component reaction of aryldiazonium tetrafluoroborates, sulfur dioxide, 1,2-dibromoethane, and hydrazines under metal-free conditions is described, leading to 2-arylsulfonyl hydrazones. This transformation proceeds via insertion of sulfur dioxide with good functional group tolerance.

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C–H bond sulfonylation of anilines with the insertion of sulfur dioxide under metal-free conditions

Chemical Communications ◽

10.1039/c8cc03465f ◽

2018 ◽

Vol 54 (54) ◽

pp. 7459-7462 ◽

Cited By ~ 32

Author(s):

Kaida Zhou ◽

Jun Zhang ◽

Lifang Lai ◽

Jiang Cheng ◽

Jiangtao Sun ◽

...

Keyword(s):

Sulfur Dioxide ◽

Metal Catalysts ◽

Metal Free ◽

Mild Conditions ◽

Three Component Reaction

2-Sulfonylanilines are generated in moderate to good yields through a three-component reaction of anilines, DABCO·(SO2)2, and aryldiazonium tetrafluoroborates under mild conditions. No metal catalysts or additives are needed for this transformation.

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Photoinduced synthesis of 2-sulfonylacetonitriles with the insertion of sulfur dioxide under ultraviolet irradiation

Chemical Communications ◽

10.1039/d0cc00351d ◽

2020 ◽

Vol 56 (17) ◽

pp. 2554-2557 ◽

Cited By ~ 14

Author(s):

Kaida Zhou ◽

Jin-Biao Liu ◽

Wenlin Xie ◽

Shengqing Ye ◽

Jie Wu

Keyword(s):

Sulfur Dioxide ◽

Ultraviolet Irradiation ◽

Room Temperature ◽

Metal Free ◽

Alkyl Iodides ◽

Photoinduced Synthesis

Metal-free insertion of sulfur dioxide with aryl/alkyl iodides and 3-azido-2-methylbut-3-en-2-ol under ultraviolet irradiation at room temperature is achieved, giving rise to 2-sulfonylacetonitriles in moderate to good yields.

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Metal-Free Sulfonylative Annulations of Alkyl Diiodides with Sulfur Dioxide: Synthesis of Cyclic Aliphatic Sulfones

Organic Chemistry Frontiers ◽

10.1039/d1qo00804h ◽

2021 ◽

Author(s):

Xiuwen Jia ◽

Chunxi Huang ◽

Xuemei Zhang ◽

Zhong Lian

Keyword(s):

Sulfur Dioxide ◽

Metal Free ◽

Gaseous Sulfur

A straightforward protocol for cyclic aliphatic sulfones is effectively established via sulfonylative annulations of alkyl diiodides and gaseous sulfur dioxide. In this transformation, SOgen serves as a safe, bench-stable and...

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Visible-light promoted one-pot synthesis of sulfonated spiro[4,5]trienones from propiolamides, anilines and sulfur dioxide under transition metal-free conditions

Chemical Communications ◽

10.1039/c9cc05949k ◽

2019 ◽

Vol 55 (81) ◽

pp. 12212-12215 ◽

Cited By ~ 11

Author(s):

Yu Liu ◽

Qiao-Lin Wang ◽

Zan Chen ◽

Quan Zhou ◽

Bi-Quan Xiong ◽

...

Keyword(s):

Sulfur Dioxide ◽

Transition Metal ◽

Visible Light ◽

Aromatic Amines ◽

One Pot ◽

Metal Free ◽

One Pot Synthesis

A novel visible-light promoted sulfonylation/ipso-cyclization of N-arylpropiolamides with aromatic amines and DABCO·(SO2)2 to synthesize various sulfonated spiro[4,5]trienones is reported.

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