Recent advances in benzylic and heterobenzylic lithiation

Autor:	Graeme Barker, Jeff Y. F. Wong
Rok vydání:	2020
Předmět:	chemistry.chemical_compound chemistry 010405 organic chemistry Aryl Organic Chemistry Drug Discovery 010402 general chemistry 01 natural sciences Biochemistry Combinatorial chemistry Small molecule 0104 chemical sciences
Zdroj:	Tetrahedron. 76:131704
ISSN:	0040-4020
DOI:	10.1016/j.tet.2020.131704
Popis:	Aryl and heteroaryl rings are omnipresent in small molecule drugs, and examples bearing multiple substitutions at benzylic positions are ubiquitous across a range of pharmaceutical families. The comparative acidity of α-aryl protons makes organolithium mediated deprotonation-substitution protocols an attractive strategy for effecting substitutions at benzylic positions. In this review, we survey recent advances in benzylic lithiation chemistry, including 1) lithiations facilitated by heteroatom-appended directing groups, 2) lateral lithiations enabled by directing groups attached in the aryl ortho-position, as well as 3) examples remote from any Lewis basic group. Recent 4) heterobenzylic and 5) stereoselective benzylic lithiations are also summarized.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::8c9ae8e196a075b5d68367ab8254ef26 https://doi.org/10.1016/j.tet.2020.131704 Zobrazit plný text záznamu Full Text from ScienceDirect