Ligand effects, solvent cooperation, and large kinetic solvent deuterium isotope effects in gold(I)-catalyzed intramolecular alkene hydroamination

• Ruichen Lan,
• Brock Yager,
• Yoonsun Jee,
• Cynthia S. Day and
• Amanda C. Jones

Beilstein J. Org. Chem. 2024, 20, 479–496, doi:10.3762/bjoc.20.43

• here. Previous discussions of solvent effects focus on the ability to support or disrupt substrate metal interactions. Acetonitrile was shown to coordinate to gold more strongly than C–C multiple bonds, thus highly disfavoring the necessary π-coordination to initiate reactivity, and acetonitrile

Recent advances in Cu-catalyzed C(sp³)–Si and C(sp³)–B bond formation

• Balaram S. Takale,
• Ruchita R. Thakore,
• Elham Etemadi-Davan and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2020, 16, 691–737, doi:10.3762/bjoc.16.67

• to optically active secondary alcohols (e.g., 342, Scheme 54) [97]. 2.2 Regioselective borylation of alkynes, alkenes, and allenes Cu-catalyzed borylation of C–C multiple bonds involves the formation of nucleophilic Cu–B species that coordinate with a π-system to initially transfer the boryl group

Controlling alkyne reactivity by means of a copper-catalyzed radical reaction system for the synthesis of functionalized quaternary carbons

• Goki Hirata,
• Yu Yamane,
• Naoya Tsubaki,
• Reina Hara and
• Takashi Nishikata

Beilstein J. Org. Chem. 2020, 16, 502–508, doi:10.3762/bjoc.16.45

• alkene derivatives. Because an alkyne undergoes addition reaction at a C–C triple bond or cross-coupling at a terminal C–H bond. Combining those reaction patterns could realize a new reaction methodology to synthesize complex molecules including C–C multiple bonds. In this report, we found that the

β-Hydroxy sulfides and their syntheses

• Mokgethwa B. Marakalala,
• Edwin M. Mmutlane and
• Henok H. Kinfe

Beilstein J. Org. Chem. 2018, 14, 1668–1692, doi:10.3762/bjoc.14.143

• 105–109 (Scheme 40) [73]. 3.5 Other synthetic routes to β-hydroxy sulfides Incorporation of amine, silyl and sulfide functional groups into C–C multiple bonds offers an attractive route to appropriately functionalized substrates. Inter- and intramolecular thiol-ene reaction is a highly efficient, free

Cross-dehydrogenative coupling for the intermolecular C–O bond formation

• Igor B. Krylov,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2015, 11, 92–146, doi:10.3762/bjoc.11.13

• the intermolecular formation of new bonds between the starting molecules. For instance, such reactions involve the oxidation of several C–H bonds, the elimination not only of hydrogen atoms but also of other moieties from the starting molecules, the addition at C–C multiple bonds, and so on. The cross

New developments in gold-catalyzed manipulation of inactivated alkenes

• Michel Chiarucci and
• Marco Bandini

Beilstein J. Org. Chem. 2013, 9, 2586–2614, doi:10.3762/bjoc.9.294

• intends to summarize the recent progresses in the field, with particular emphasis on mechanistic details. Keywords: alkene; gold catalysis; mechanism; organic synthesis; Review 1 Introduction Homogeneous gold catalysis is emerged as one of the most powerful means for the activation of C–C multiple bonds

• normally activated equivalents, like halides, acetates, carbonates and phosphates are employed in metal-catalyzed Tsuji–Trost type alkylation [14][15]. 2 Formation of C–O bonds 2.1 Mechanistic considerations The addition of oxygen-based nucleophiles to C–C multiple bonds is an effective and atom-economical

• point of view [33]. Although many metal and Brønsted acid assisted processes have been documented the high functional group tolerance of gold complexes combined with their high efficiency in the electrophilic activation of C–C multiple bonds have made gold catalysis an important tool for the

Intramolecular hydroamination of alkynic sulfonamides catalyzed by a gold–triethynylphosphine complex: Construction of azepine frameworks by 7-exo-dig cyclization

• Hideto Ito,
• Tomoya Harada,
• Hirohisa Ohmiya and
• Masaya Sawamura

Beilstein J. Org. Chem. 2011, 7, 951–959, doi:10.3762/bjoc.7.106

• for the construction of N-heterocyclic compounds, metal-catalyzed intramolecular hydroamination of unactivated C–C multiple bonds is particularly straightforward and efficient [17][18]. Specifically, gold-catalyzed intramolecular hydroaminations of alkynes, alkenes and allenes show remarkable

Recent advances in the gold-catalyzed additions to C–C multiple bonds

• He Huang,
• Yu Zhou and
• Hong Liu

Beilstein J. Org. Chem. 2011, 7, 897–936, doi:10.3762/bjoc.7.103

• compounds, ranging from pharmaceuticals and agrochemicals to advanced materials and polymers. Cationic gold acts as a soft and carbophilic Lewis acid and is considered one of the most powerful activators of C–C multiple bonds. Consequently, gold-catalysis plays an important role in the development of new

• strategies to form these bonds in more convenient ways. In this review, we highlight recent advances in the gold-catalyzed chemistry of addition of X–H (X = O, N, C) bonds to C–C multiple bonds, tandem reactions, and asymmetric additions. This review covers gold-catalyzed organic reactions published from

• 2008 to the present. Keywords: asymmetric addition; catalysis; gold; C−C multiple bonds; tandem reaction; Review 1 Introduction Gold-catalyzed reactions have emerged as a powerful synthetic tool in modern organic synthesis. This past decade has been the boom time for homogeneous gold catalysis, which