Open AccessDecatungstate-Catalyzed C(sp3)–H Sulfinylation: Rapid Access to Diverse Organosulfur Functionality
Author(s) -
Patrick Sarver,
Noah B. Bissonnette,
David W. C. MacMillan
Publication year - 2021
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.1c04722
Subject(s) - chemistry , organosulfur compounds , sulfinic acid , sulfur , catalysis , combinatorial chemistry , alkyl , photocatalysis , molecule , organic chemistry
Here we report the direct conversion of strong, aliphatic C( sp 3 )-H bonds into the corresponding alkyl sulfinic acids via decatungstate photocatalysis. This transformation has been applied to a diverse range of C( sp 3 )-rich scaffolds, including natural products and approved pharmaceuticals, providing efficient access to complex sulfur-containing products. To demonstrate the broad potential of this methodology for the divergent synthesis of pharmaceutically relevant molecules, procedures for the diversification of the sulfinic acid products into a range of medicinally relevant functional groups have been developed.