/ Home
/ SUBMISSION

/ The BJOC
/ Diamond Open Access
/ Journal Statistics
/ Editorial Board
/ Community
/ Call for papers

/ Latest Articles
/ Most accessed
/ Thematic issues
/ Volumes
/ Authors

/ E-Alerts

/ TWITTER
/ LINKEDIN
/ Mastodon
/ RSS FEED

Empty search

Article Type

Publication Date Range

Search Tips

This search combines search strings from the content search (i.e. "Full Text", "Author", "Title", "Abstract", or "Keywords") with "Article Type" and "Publication Date Range" using the AND operator.

Search Examples

aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)

Search results

Search for "heteroatom-mixed system" in Full Text gives 1 result(s) in Beilstein Journal of Organic Chemistry.

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

Akiya Ogawa and
Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

with a variety of heteroatoms. In this Perspective, we review the addition and cyclization reactions of heteroatom radicals with isocyanides and discuss the synthetic prospects of the reaction of isocyanides with heteroatom radicals. Keywords: aza-Bergman cyclization; heteroatom-mixed system; imidoyl

PDF

Graphical Abstract

Figure 1: Resonance structures and reactivity of carbon monoxide.

Jump to Figure 1

Figure 2: Resonance structures and reactivity of isocyanides.

Jump to Figure 2

Scheme 1: Possible three pathways of the E• formation for imidoylation.

Jump to Scheme 1

Scheme 2: Radical addition of thiols to isocyanides.

Jump to Scheme 2

Scheme 3: Selective thioselenation and catalytic dithiolation of isocyanides.

Jump to Scheme 3

Scheme 4: Synthesis of carbacephem framework.

Jump to Scheme 4

Scheme 5: Sequential addition of (PhSe)₂ to ethyl propiolate and isocyanide.

Jump to Scheme 5

Scheme 6: Isocyanide insertion reaction into carbon-tellurium bonds.

Jump to Scheme 6

Scheme 7: Radical addition to isocyanides with disubstituted phosphines.

Jump to Scheme 7

Scheme 8: Radical addition to phenyl isocyanides with diphosphines.

Jump to Scheme 8

Scheme 9: Radical reaction of tin hydride and hydrosilane toward isocyanide.

Jump to Scheme 9

Scheme 10: Isocyanide insertion into boron compounds.

Jump to Scheme 10

Scheme 11: Isocyanide insertion into cyclic compounds containing boron units.

Jump to Scheme 11

Scheme 12: Photoinduced hydrodefunctionalization of isocyanides.

Jump to Scheme 12

Scheme 13: Tin hydride-mediated indole synthesis and cross-coupling.

Jump to Scheme 13

Scheme 14: 2-Thioethanol-mediated radical cyclization of alkenyl isocyanide.

Jump to Scheme 14

Scheme 15: Thiol-mediated radical cyclization of o-alkenylaryl isocyanide.

Jump to Scheme 15

Scheme 16: (PhTe)₂-assisted dithiolative cyclization of o-alkenylaryl isocyanide.

Jump to Scheme 16

Scheme 17: Trapping imidoyl radicals with heteroatom moieties.

Jump to Scheme 17

Scheme 18: Trapping imidoyl radicals with isocyano group.

Jump to Scheme 18

Scheme 19: Quinoline synthesis via aza-Bergman cyclization.

Jump to Scheme 19

Scheme 20: Phenanthridine synthesis via radical cyclization of 2-isocyanobiaryls.

Jump to Scheme 20

Scheme 21: Phenanthridine synthesis by radical reactions with AIBN, DBP and TTMSS.

Jump to Scheme 21

Scheme 22: Phenanthridine synthesis by oxidative cyclization of 2-isocyanobiaryls.

Jump to Scheme 22

Scheme 23: Phenanthridine synthesis using a photoredox system.

Jump to Scheme 23

Scheme 24: Phenanthridine synthesis induced by phosphorus-centered radicals.

Jump to Scheme 24

Scheme 25: Phenanthridine synthesis induced by sulfur-centered radicals.

Jump to Scheme 25

Scheme 26: Phenanthridine synthesis induced by boron-centered radicals.

Jump to Scheme 26

Scheme 27: Phenanthridine synthesis by oxidative cyclization of 2-aminobiaryls.

Jump to Scheme 27

Album

Perspective

Published 26 Aug 2024

Full text

Other Beilstein-Institut Open Science Activities

/ Help / Support & Contact / E-Alerts / Privacy Policy / Terms & Conditions / Impressum