Photocatalytic Reaction of Aryl Halides with Tin(II) Acetate to Generate Arylstannane(IV) Reagents

Photocatalytic Reaction of Aryl Halides with Tin(II) Acetate to Generate Arylstannane(IV) Reagents Full article

Journal

ACS Catalysis
ISSN: 2155-5435

Output data

Year: 2023, Volume: 13, Number: 19, Pages: 12766-12773 Pages count : 8 DOI: 10.1021/acscatal.3c03626

Authors

Zemtsov Artem A. ¹ , Supranovich Vyacheslav I. ¹ , Levin Vitalij V. ¹ , Dilman Alexander D. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation

Aromatic organotin(IV) compounds are a valuable class of reagents widely used in cross-coupling reactions. However, the toxicity of the most popular tributyl-substituted arylstannanes, combined with complicated methods for their synthesis, imposes serious limitations. Herein, we report an approach to accessing aryl organotin(IV) reagents directly from aryl halides and cheap inorganic tin(II) acetate. The insertion of tin(II) into the carbon–halogen bond is performed under photocatalytic conditions and proceeds through the generation of aryl radicals. The resulting organotin reagents may be directly employed in Migita–Kosugi–Stille cross-coupling or can be converted into conventional tributyltin compounds by treatment with butylzinc bromide.

Zemtsov A.A. , Supranovich V.I. , Levin V.V. , Dilman A.D.
Photocatalytic Reaction of Aryl Halides with Tin(II) Acetate to Generate Arylstannane(IV) Reagents
ACS Catalysis. 2023. V.13. N19. P.12766-12773. DOI: 10.1021/acscatal.3c03626 WOS Scopus OpenAlex

Web of science:	WOS:001068476700001
Scopus:	2-s2.0-85174736761
OpenAlex:	W4386767176

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OpenAlex	6
Scopus	6
Web of science	3