An Iodine-catalysing process for an efficient and scalable sulfenylation protocol for indoles employing aryl-/ alkyl sulfonyl chlorides has been developed. A series of sterically and electronically divergent aryl-/ alkyl sulfonyl chlorides were participated in the sulfenylation of C(sp 2 )-H bonds, resulting in a high to excellent yield of indole 3-sulfenylether molecules. It is noteworthy that indole-3thiomethyl ether is efficiently generated with methanesulfonyl chloride as an electrophile, indicating the potential of this methodology.
Aerobic dehydrogenative sulfenylation of H-phosphonites, and phosphine oxides with aryl/alkylsulfonyl hydrazides catalyzed by a sub-stoichiometric amount of copper iodide has been accomplished. This protocol is compatible with functional groups, and results in various thiophosphate derivatives in good to high yields.
Synthesis of the natural product calcaripeptide C derived from the fungal metabolite mycelium KF525 of Calcarisporium sp. has been achieved. This complementary approach avoids the use of a stoichiometric amount of chiral auxiliary reagents as commonly used to generate enantioenriched advanced precursors. The enantioselective synthesis of calcaripeptide C is remarkable in that using catalytic reactions sets the two stereogenic centers efficiently with good levels of enantioselectivity. Further diversification of the calcaripeptide C structures is possible by employing a complementary catalytic enantioenriched Ru-catalyst.
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