Bioinspired Photoredox Benzylation of Quinones

نویسندگان

چکیده

3-Benzylmenadiones were obtained in good yield by using a blue-light-induced photoredox process the presence of Fe(III), oxygen, and γ-terpinene acting as hydrogen-atom transfer agent. This methodology is compatible with wide variety diversely substituted 1,4-naphthoquinones well various cheap, readily available benzyl bromides excellent functional group tolerance. The benzylation mechanism was investigated supports three-step radical cascade key involvement photogenerated superoxide anion radical.

برای دانلود باید عضویت طلایی داشته باشید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Enantioselective α-benzylation of aldehydes via photoredox organocatalysis.

The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantiosele...

متن کامل

Cooperative Electronic and Structural Regulation in a Bioinspired Allosteric Photoredox Catalyst.

Herein, we report the first allosteric photoredox catalyst regulated via constructively coupled structural and electronic control. While often synergistically exploited in nature, these two types of control mechanisms have only been applied independently in the vast majority of allosteric enzyme mimics and receptors in the literature. By embedding a model of photosystem II in a supramolecular c...

متن کامل

Palladium-catalyzed benzylation of heterocyclic aromatic compounds.

Broadly applicable palladium-catalyzed heteroarene benzylation reactions are described with a focus on the most challenging heterocyclic classes under traditional benzylation techniques such as sulfur-containing heterocycles and those bearing functional groups that would be incompatible with reactions requiring Lewis acids and/or strong bases.

متن کامل

Photoredox Imino Functionalizations of Olefins

Shown herein is that polyfunctionalized nitrogen heterocycles can be easily prepared by a visible-light-mediated radical cascade process. This divergent strategy features the oxidative generation of iminyl radicals and subsequent cyclization/radical trapping, which allows the effective construction of highly functionalized heterocycles. The reactions proceed efficiently at room temperature, uti...

متن کامل

Reaction of Quinones with Nitrosoarenes

Formation of the 2,3-dicyanohydroquinone (3) can be rationalised in terms of preferential addition of cyanide at the most electron deficient unsubstituted carbon of the cyanoquinone (2 ) in the same way as alcohols and other nucleophiles add to the 3-position of the acylquinone ( 8 ) [4], However, such an argu­ ment could not be applied to the formation of the dihydroxylamine (6 ). Hence, eithe...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

ژورنال

عنوان ژورنال: Journal of Organic Chemistry

سال: 2021

ISSN: ['1520-6904', '0022-3263']

DOI: https://doi.org/10.1021/acs.joc.1c00814