What were the main reasons for the enslavement of Africans in the Caribbean in the 14th century?
African slavery in the Caribbean did not begin until the early sixteenth century; so there was no slavery of that type anywhere in North America in the 14th Century. No European or African presence is noted in North America before 1492.
However, when African slavery did take hold in the Caribbean, it was because of the sugar revolution in Europe. Cane sugar had been unknown in Europe until the time of the Crusades; but after its discovery, the demand for it was insatiable. Almost all the islands of the Caribbean whether occupied by the British, Spanish, French or Dutch were used for sugar cultivation. Sugar soon became the major export from the Caribbean to Europe.
Sugar cultivation is quite labor intensive, and indentured servants were insufficient to meet the demand for labor. Additionally, the life expectancy of a servant or slave on sugar plantations was quite short; as a result there was a continual demand for slaves to replace those who died. So great was the demand that several stock companies, including the Royal African Company, were organized to engage in the Caribbean slave trade for profit. Many slaves in Colonial America, particularly in South Carolina, arrived by way of the Caribbean islands.
So the sugar market in Europe was the primary reason for the transport of African slaves to the Caribbean.